chore: update yerpc 0.7.0 to 0.7.1 (#8868 )

This fixes build problems with the generated jsonrpc qt bindings which occured on UT20.04 builds (uses older qt and gcc versions) It also resolves a cargo future incompatibily warning
refactor!: remove configured_addr config
2026-10-28 15:58:22 +03:00 · 2026-10-28 11:59:47 +01:00 · 2026-10-27 11:22:52 +00:00 · 2026-10-26 16:28:40 +00:00 · 2026-10-26 14:05:11 +00:00 · 2026-10-26 15:00:44 +01:00
79 changed files with 1739 additions and 1409 deletions
@@ -25,6 +25,8 @@ env:
  # Minimum Supported Rust Version
  MSRV: 1.89.0

+  PYTHON_VERSION: "3.15"
+
 jobs:
  lint_rust:
    name: Lint Rust
@@ -268,11 +270,11 @@ jobs:
      fail-fast: false
      matrix:
        include:
-          # Currently used Rust version.
+          # Currently used Python version.
          - os: ubuntu-latest
-            python: 3.14
+            python: latest
          - os: macos-latest
-            python: 3.14
+            python: latest

          # PyPy tests
          - os: ubuntu-latest
@@ -303,7 +305,7 @@ jobs:
      - name: Install python
        uses: actions/setup-python@v7.0.0
        with:
-          python-version: ${{ matrix.python }}
+          python-version: ${{ matrix.python == 'latest' && env.PYTHON_VERSION || matrix.python }}

      - name: Install tox
        run: pip install tox
@@ -324,11 +326,11 @@ jobs:
      matrix:
        include:
          - os: ubuntu-latest
-            python: 3.14
+            python: latest
          - os: macos-latest
-            python: 3.14
+            python: latest
          - os: windows-latest
-            python: 3.14
+            python: latest

          # PyPy tests
          - os: ubuntu-latest
@@ -351,7 +353,7 @@ jobs:
      - name: Install python
        uses: actions/setup-python@v7.0.0
        with:
-          python-version: ${{ matrix.python }}
+          python-version: ${{ matrix.python == 'latest' && env.PYTHON_VERSION || matrix.python }}

      - name: Install tox
        run: pip install tox
@@ -1,5 +1,71 @@
 # Changelog

+## [2.65.0] - 2026-10-22
+
+### Features / Changes
+
+- show info message for unpinning ([#8852](https://github.com/chatmail/core/pull/8852)).
+
+### Fixes
+
+- don't ignore `join_next()` errors in `background_fetch_any()`.
+
+### Documentation
+
+- remove outdated sentence saying QR scan aborts started securejoin processes.
+
+### Miscellaneous Tasks
+
+- update webpki-roots to 1.0.10.
+- update webpki-roots 0.26.8 to 0.26.11.
+- update rustls-webpki 0.103.15 to 0.103.16.
+- add deny.toml exception for RUSTSEC-2026-0382.
+- remove unused broadcast icon.
+
+### Refactor
+
+- make `message::insert_tombstone()` synchronous.
+- make `insert_into_smtp()` synchronous.
+- make `non_chat_headers()` synchronous.
+- create all keyupdates in a single transaction.
+
+## [2.64.0] - 2026-10-20
+
+### API-Changes
+
+- add jsonrpc for `get_summary_text`.
+
+### Features / Changes
+
+- take key flags and expiration into account when selecting the key.
+- switch to another SMTP transport when current one returns an error.
+- do not spam channel summaries with reactions ([#8829](https://github.com/chatmail/core/pull/8829)).
+- do not copy Chat-Version header into unprotected headers.
+
+### Fixes
+
+- Encode '@' with '%40' again in QR codes ([#8825](https://github.com/chatmail/core/pull/8825)).
+- abort scheduler tasks after shutdown timeout ([#8832](https://github.com/chatmail/core/pull/8832)).
+- do not apply channel reaction summaries as reactions.
+- imap: do not busy loop if there are no connection candidates and interrupt channel is closed.
+- races in `get_summary_text_ext`, improve perf.
+- avoid integer overflow when multiplying received image width by height.
+
+### CI
+
+- test with Python 3.15.
+
+### Miscellaneous Tasks
+
+- bump rustls from 0.23.45 to 0.23.46.
+
+### Refactor
+
+- remove Context argument from `secret_key_to_public_key()`.
+- smtp: introduce smtp::Connection structure.
+- move `call_state_ext` to `CallInfo`.
+- clean up remaining `clippy::arithmetic_side_effects` in `mimeparser`.
+
 ## [2.63.0] - 2026-10-09

 ### API-Changes
@@ -8983,3 +9049,5 @@ https://github.com/chatmail/core/pulls?q=is%3Apr+is%3Aclosed
 [2.61.0]: https://github.com/chatmail/core/compare/v2.60.0..v2.61.0
 [2.62.0]: https://github.com/chatmail/core/compare/v2.61.0..v2.62.0
 [2.63.0]: https://github.com/chatmail/core/compare/v2.62.0..v2.63.0
+[2.64.0]: https://github.com/chatmail/core/compare/v2.63.0..v2.64.0
+[2.65.0]: https://github.com/chatmail/core/compare/v2.64.0..v2.65.0
@@ -334,13 +334,13 @@ dependencies = [

 [[package]]
 name = "async-trait"
-version = "0.1.86"
+version = "0.1.92"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "644dd749086bf3771a2fbc5f256fdb982d53f011c7d5d560304eafeecebce79d"
+checksum = "82f6aeea286b8eb4dd3431a1be1b59d290ace00f5bfd8e2a159bc2a05e2c1667"
 dependencies = [
 "proc-macro2",
 "quote",
- "syn 2.0.118",
+ "syn 3.0.6",
 ]

 [[package]]
@@ -920,9 +920,9 @@ checksum = "f46ad14479a25103f283c0f10005961cf086d8dc42205bb44c46ac563475dca6"

 [[package]]
 name = "clipboard-win"
-version = "5.4.0"
+version = "5.4.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "15efe7a882b08f34e38556b14f2fb3daa98769d06c7f0c1b076dfd0d983bc892"
+checksum = "052af7878466feccda12ba7a6a67d019d712f296809559b47c12c8cc196d3a9a"
 dependencies = [
 "error-code",
 ]
@@ -1334,7 +1334,7 @@ dependencies = [

 [[package]]
 name = "deltachat"
-version = "2.63.0"
+version = "2.66.0-dev"
 dependencies = [
 "anyhow",
 "astral-tokio-tar",
@@ -1415,7 +1415,7 @@ dependencies = [
 "url",
 "uuid",
 "walkdir",
- "webpki-roots",
+ "webpki-roots 1.0.10",
 ]

 [[package]]
@@ -1440,7 +1440,7 @@ dependencies = [

 [[package]]
 name = "deltachat-jsonrpc"
-version = "2.63.0"
+version = "2.66.0-dev"
 dependencies = [
 "anyhow",
 "async-channel 2.5.0",
@@ -1461,14 +1461,14 @@ dependencies = [

 [[package]]
 name = "deltachat-jsonrpc-bindings"
-version = "2.63.0"
+version = "2.66.0-dev"
 dependencies = [
 "deltachat-jsonrpc",
 ]

 [[package]]
 name = "deltachat-repl"
-version = "2.63.0"
+version = "2.66.0-dev"
 dependencies = [
 "anyhow",
 "deltachat",
@@ -1484,7 +1484,7 @@ dependencies = [

 [[package]]
 name = "deltachat-rpc-server"
-version = "2.63.0"
+version = "2.66.0-dev"
 dependencies = [
 "anyhow",
 "deltachat",
@@ -1514,7 +1514,7 @@ dependencies = [

 [[package]]
 name = "deltachat_ffi"
-version = "2.63.0"
+version = "2.66.0-dev"
 dependencies = [
 "anyhow",
 "deltachat",
@@ -2695,7 +2695,7 @@ dependencies = [
 "tokio",
 "tokio-rustls",
 "tower-service",
- "webpki-roots",
+ "webpki-roots 0.26.11",
 ]

 [[package]]
@@ -3060,7 +3060,7 @@ dependencies = [
 "tracing",
 "url",
 "wasm-bindgen-futures",
- "webpki-roots",
+ "webpki-roots 0.26.11",
 "x509-parser",
 "z32",
 ]
@@ -3246,7 +3246,7 @@ dependencies = [
 "tokio-websockets",
 "tracing",
 "url",
- "webpki-roots",
+ "webpki-roots 0.26.11",
 "ws_stream_wasm",
 "z32",
 ]
@@ -5132,7 +5132,7 @@ dependencies = [
 "wasm-bindgen-futures",
 "wasm-streams",
 "web-sys",
- "webpki-roots",
+ "webpki-roots 0.26.11",
 "windows-registry",
 ]

@@ -5289,9 +5289,9 @@ dependencies = [

 [[package]]
 name = "rustls"
-version = "0.23.45"
+version = "0.23.46"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "0d41d731c7d2f962d1ccc364cec258de3c0e93b38c2fb3ba97ac74513048d634"
+checksum = "48e13bd8c0e9365c43cfa5c9e8f9ad49d3c8444926c9aac819e0e4dc503c8fdf"
 dependencies = [
 "brotli",
 "brotli-decompressor",
@@ -5299,7 +5299,7 @@ dependencies = [
 "once_cell",
 "ring",
 "rustls-pki-types",
- "rustls-webpki 0.103.15",
+ "rustls-webpki 0.103.16",
 "subtle",
 "zeroize",
 ]
@@ -5336,9 +5336,9 @@ dependencies = [

 [[package]]
 name = "rustls-webpki"
-version = "0.103.15"
+version = "0.103.16"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f3c3cf1d8b1e7d4927e2d154c3fcb02979afb9939629c62cd9048d4f07b60ac2"
+checksum = "4443b1b6d39d7c663139942cc4558262562d2c84123bb6282ef177009ca8b281"
 dependencies = [
 "ring",
 "rustls-pki-types",
@@ -6309,9 +6309,9 @@ checksum = "1f3ccbac311fea05f86f61904b462b55fb3df8837a366dfc601a0161d0532f20"

 [[package]]
 name = "tokio"
-version = "1.53.1"
+version = "1.53.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "202caea871b69668250d242070849eb495be178ed697a3e98aebce5bc81a0bed"
+checksum = "ce3335fa71841cda333a58d7615b03901380ecf09d59b3296d21f8bbac0dde4e"
 dependencies = [
 "bytes",
 "libc",
@@ -6923,9 +6923,18 @@ dependencies = [

 [[package]]
 name = "webpki-roots"
-version = "0.26.8"
+version = "0.26.11"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2210b291f7ea53617fbafcc4939f10914214ec15aace5ba62293a668f322c5c9"
+checksum = "521bc38abb08001b01866da9f51eb7c5d647a19260e00054a8c7fd5f9e57f7a9"
+dependencies = [
+ "webpki-roots 1.0.10",
+]
+
+[[package]]
+name = "webpki-roots"
+version = "1.0.10"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "1c1c8e20c8a38fc7d65abfe74eb7280e4aa667e8eec8bc84996d2874810748d9"
 dependencies = [
 "rustls-pki-types",
 ]
@@ -7521,9 +7530,9 @@ dependencies = [

 [[package]]
 name = "yerpc"
-version = "0.7.0"
+version = "0.7.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6924db1f1011f1d22566c45c7090aa66c3107c3c463ca32beaa8b2327127040a"
+checksum = "3d7436d4f59711e0a796697630a77c33981c4b5406bdd52e874a08b27ad938ee"
 dependencies = [
 "anyhow",
 "async-channel 1.9.0",
@@ -7541,9 +7550,9 @@ dependencies = [

 [[package]]
 name = "yerpc_derive"
-version = "0.7.0"
+version = "0.7.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "42c374248c189b15a7f0660db3984e9dcc790ec15f4b44e932e92be49de829f9"
+checksum = "feab3bc81a5743c3661099ef6727b182a27c32686b78831e143786b636b32fee"
 dependencies = [
 "convert_case",
 "darling",
@@ -1,6 +1,6 @@
 [package]
 name = "deltachat"
-version = "2.63.0"
+version = "2.66.0-dev"
 edition = "2024"
 license = "MPL-2.0"
 rust-version = "1.89"
@@ -107,7 +107,7 @@ toml = "0.9"
 url = "2"
 uuid = { version = "1", features = ["serde", "v4"] }
 walkdir = "2.5.0"
-webpki-roots = "0.26.8"
+webpki-roots = "1.0.10"

 [dev-dependencies]
 anyhow = { workspace = true, features = ["backtrace"] } # Enable `backtrace` feature in tests.
@@ -1,149 +0,0 @@
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@@ -31,7 +31,7 @@ use deltachat::internals_for_benches::create_broadcast_secret;
 use deltachat::internals_for_benches::save_broadcast_secret;
 use deltachat::securejoin::get_securejoin_qr;
 use deltachat::{
-    Events, chat::ChatId, config::Config, context::Context, internals_for_benches::key_from_asc,
+    Events, chat::ChatId, context::Context, internals_for_benches::key_from_asc,
    internals_for_benches::parse_and_get_text, internals_for_benches::store_self_keypair,
    stock_str::StockStrings,
 };
@@ -57,10 +57,6 @@ async fn create_context() -> Context {
        .await
        .unwrap();

-    context
-        .set_config(Config::ConfiguredAddr, Some("bob@example.net"))
-        .await
-        .unwrap();
    let secret = key_from_asc(include_str!("../test-data/key/bob-secret.asc")).unwrap();
    store_self_keypair(&context, &secret)
        .await
@@ -5,7 +5,6 @@ use std::path::PathBuf;
 use criterion::{Criterion, criterion_group, criterion_main};
 use deltachat::{
    Events,
-    config::Config,
    context::Context,
    imex::{ImexMode, imex},
    receive_imf::receive_imf,
@@ -109,16 +108,6 @@ async fn create_context() -> Context {
            .unwrap();
    }

-    let addr = "alice@example.com";
-    context.set_config(Config::Addr, Some(addr)).await.unwrap();
-    context
-        .set_config(Config::ConfiguredAddr, Some(addr))
-        .await
-        .unwrap();
-    context
-        .set_config(Config::Configured, Some("1"))
-        .await
-        .unwrap();
    context
 }

@@ -1,6 +1,6 @@
 [package]
 name = "deltachat_ffi"
-version = "2.63.0"
+version = "2.66.0-dev"
 description = "Deltachat FFI"
 edition = "2024"
 license = "MPL-2.0"
@@ -389,9 +389,6 @@ char*           dc_get_blobdir               (const dc_context_t* context);
 /**
 * Configure the context. The configuration is handled by key=value pairs as:
 *
- * - `configured_addr` = Email address in use.
- *                    Unless for testing, do not set this value using dc_set_config().
- *                    Instead, set `addr` and call dc_configure().
 * - `displayname`  = Own name to use when sending messages. MUAs are allowed to spread this way e.g. using CC, defaults to empty
 * - `selfstatus`   = Own status to display, e.g. in e-mail footers, defaults to empty
 * - `selfavatar`   = File containing avatar. Will immediately be copied to the 
@@ -468,9 +465,6 @@ char*           dc_get_blobdir               (const dc_context_t* context);
 *                    e.g. `ui.desktop.foo`, `ui.desktop.linux.bar`, `ui.android.foo`, `ui.dc40.bar`, `ui.bot.simplebot.baz`.
 *                    These keys go to backups and allow easy per-account settings when using @ref dc_accounts_t,
 *                    however, are not handled by the core otherwise.
- * - `webxdc_realtime_enabled` = Whether the realtime APIs should be enabled.
- *                               0 = WebXDC realtime API is disabled and behaves as noop.
- *                               1 = WebXDC realtime API is enabled (default).
 * - `who_can_call_me` = Who can cause call notifications.
 *                       0 = Everybody (except explicitly blocked contacts),
 *                       1 = Contacts (default, does not include contact requests),
@@ -481,8 +475,6 @@ char*           dc_get_blobdir               (const dc_context_t* context);
 * if you want to use the deprecated dc_configure() API, such as:
 *
 * - `addr`         = Email address to use for configuration.
- *                    If dc_configure() fails this is not the email address actually in use.
- *                    Use `configured_addr` to find out the email address actually in use.
 * - `mail_server`  = IMAP-server, guessed if left out
 * - `mail_user`    = IMAP-username, guessed if left out
 * - `mail_pw`      = IMAP-password (always needed)
@@ -2613,8 +2605,6 @@ char*           dc_get_securejoin_qr_svg         (dc_context_t* context, uint32_
 * During the handshake, info messages are added to the chat,
 * showing progress, success or errors.
 *
- * Subsequent calls of dc_join_securejoin() will abort previous, unfinished handshakes.
- *
 * See https://securejoin.delta.chat/ for details about both protocols.
 *
 * @memberof dc_context_t
@@ -4478,6 +4468,7 @@ int             dc_msg_is_info                (const dc_msg_t* msg);
 * - DC_INFO_CHAT_E2EE (50) - Info-message for "Chat is end-to-end-encrypted"
 * - DC_INFO_GROUP_DESCRIPTION_CHANGED (70) - Info-message "Description changed", UI should open the profile with the description
 * - DC_INFO_MESSAGE_PINNED (71) - Message pinned, UI should scroll to the pinned message returned by dc_msg_get_parent()
+ * - DC_INFO_MESSAGE_UNPINNED (72) - Message unpinned, UI should scroll to the pinned message returned by dc_msg_get_parent()
 *
 * For the messages that refer to a CONTACT,
 * dc_msg_get_info_contact_id() returns the contact ID.
@@ -4538,6 +4529,7 @@ uint32_t        dc_msg_get_info_contact_id    (const dc_msg_t* msg);
 #define         DC_INFO_CHAT_E2EE                 50
 #define         DC_INFO_GROUP_DESCRIPTION_CHANGED 70
 #define         DC_INFO_MESSAGE_PINNED            71
+#define         DC_INFO_MESSAGE_UNPINNED          72


 /**
@@ -6474,7 +6466,7 @@ void dc_event_unref(dc_event_t* event);
 * The event is emitted on the device modifying the transports
 * as well as on other devices applying the synced change,
 * for the JSON-RPC calls `add_or_update_transport`, `add_transport_from_qr`,
- * `delete_transport` or `set_config(configured_addr)`.
+ * `delete_transport`.
 */
 #define DC_EVENT_TRANSPORTS_MODIFIED           2600

@@ -7275,6 +7267,12 @@ void dc_event_unref(dc_event_t* event);
 /// @deprecated 2026-08-31
 #define DC_STR_PHASING_OUT 245

+/// "You unpinned a message."
+#define DC_STR_MESSAGE_UNPINNED_BY_YOU 246
+
+/// "Message unpinned by %1$s."
+#define DC_STR_MESSAGE_UNPINNED_BY_OTHER 247
+
 /**
 * @}
 */
@@ -1,6 +1,6 @@
 [package]
 name = "deltachat-jsonrpc-bindings"
-version = "2.63.0"
+version = "2.66.0-dev"
 description = "Autogenerate DeltaChat JSON-RPC API bindings at build time"
 edition = "2024"
 license = "MPL-2.0"
@@ -54,5 +54,5 @@
  },
  "type": "module",
  "types": "dist/deltachat.d.ts",
-  "version": "2.63.0"
+  "version": "2.66.0-dev"
 }
@@ -1,6 +1,6 @@
 [package]
 name = "deltachat-jsonrpc"
-version = "2.63.0"
+version = "2.66.0-dev"
 description = "DeltaChat JSON-RPC API"
 edition = "2024"
 license = "MPL-2.0"
@@ -495,6 +495,15 @@ impl CommandApi {
        Ok(())
    }

+    /// Adds fake transport that cannot be used to connect.
+    ///
+    /// Used for offline tests only.
+    async fn add_pseudo_transport(&self, account_id: u32, addr: String) -> Result<()> {
+        let context = self.get_context(account_id).await?;
+        deltachat::transport::add_pseudo_transport(&context, &addr).await?;
+        Ok(())
+    }
+
    /// Configures a new email account using the provided parameters
    /// and adds it as a transport.
    ///
@@ -912,8 +921,6 @@ impl CommandApi {
    /// During the handshake, info messages are added to the chat,
    /// showing progress, success or errors.
    ///
-    /// Subsequent calls of `secure_join()` will abort previous, unfinished handshakes.
-    ///
    /// See https://securejoin.delta.chat/ for details about both protocols.
    ///
    /// **qr**: The text of the scanned QR code. Typically, the same string as given
@@ -1451,6 +1458,36 @@ impl CommandApi {
        MsgId::new(message_id).get_html(&ctx).await
    }

+    /// Returns a message summary.
+    /// Used for notifications, pinned messages and for copying texts to clipboard.
+    ///
+    /// - `add_forwarded`: `true`=add a hint if a message was forwarded.
+    ///    `false`=do not add the hint;
+    ///    this is allowed only if the message is shown without a username, e.g. for pinned messages.
+    /// - `add_type_emoji`: `true`=add the type of the message as an emoji prefix.
+    ///    `false`=do not add type emoji;
+    ///    this is allowed only if the message type is visible otherwise,
+    ///    close to where the emoji would be displayed otherwise
+    ///    (eg. images in pinned messages preceding summary)
+    /// - `approx_chars`: `>0`=convert linebreaks to spaces and truncate the line at about the given number of characters;
+    ///    for single-line UI elements such as pinned messages or notifications;
+    ///    additionally, UIs will most times clip the text to the available space.
+    ///    `0`=leave linebreaks as is and return the full text, useful e.g. for copying to clipboard.
+    async fn get_message_summary_text(
+        &self,
+        account_id: u32,
+        message_id: u32,
+        add_forwarded: bool,
+        add_type_emoji: bool,
+        approx_chars: u32,
+    ) -> Result<String> {
+        let ctx = self.get_context(account_id).await?;
+        let msg = Message::load_from_db(&ctx, MsgId::new(message_id)).await?;
+        Ok(msg
+            .get_summary_text_ext(&ctx, add_forwarded, add_type_emoji, approx_chars as usize)
+            .await)
+    }
+
    /// get multiple messages in one call,
    /// if loading one message fails the error is stored in the result object in it's place.
    ///
@@ -1,6 +1,6 @@
 [package]
 name = "deltachat-repl"
-version = "2.63.0"
+version = "2.66.0-dev"
 license = "MPL-2.0"
 edition = "2024"
 repository = "https://github.com/chatmail/core"
@@ -4,7 +4,7 @@ build-backend = "setuptools.build_meta"

 [project]
 name = "deltachat-rpc-client"
-version = "2.63.0"
+version = "2.66.0-dev"
 license = "MPL-2.0"
 description = "Python client for Delta Chat core JSON-RPC interface"
 classifiers = [
@@ -18,6 +18,7 @@ classifiers = [
    "Programming Language :: Python :: 3.12",
    "Programming Language :: Python :: 3.13",
    "Programming Language :: Python :: 3.14",
+    "Programming Language :: Python :: 3.15",
    "Topic :: Communications :: Chat",
    "Topic :: Communications :: Email"
 ]
@@ -139,6 +139,11 @@ class Account:
        """Add a new transport using a QR code."""
        yield self._rpc.add_transport_from_qr.future(self.id, qr)

+    @futuremethod
+    def add_pseudo_transport(self, addr: str):
+        """Add transport for offline tests without connection candidates."""
+        yield self._rpc.add_pseudo_transport.future(self.id, addr)
+
    @futuremethod
    def init_transports(self, qr: Optional[str] = None):
        """Add an initial transport on the chatmail relay that answers fastest.
@@ -376,7 +381,6 @@ class Account:

        The function returns immediately and the handshake runs in background, sending
        and receiving several messages.
-        Subsequent calls of `secure_join()` will abort previous, unfinished handshakes.
        See https://securejoin.delta.chat/ for protocol details.

        :param qrdata: The text of the scanned QR code.
@@ -87,6 +87,31 @@ def test_second_device(acf, alice_and_remote_bob) -> None:
    assert new_account.get_config("addr") == remote_eval("bob.get_config('addr')")


+def test_old_device_delete_transport(acf, alice_and_remote_bob) -> None:
+    """Test setting up old core as the second device for the new core and deleting a transport.
+
+    Old core unfortunately expects that deprecated configured_addr config value is set
+    and fails to delete a transport otherwise. The test makes sure new core sets some configured_addr
+    for backwards compatibility."""
+    alice, _alice_contact_bob, remote_eval = alice_and_remote_bob("2.62.0")
+
+    alice.set_config("displayname", "Alice123")
+    qr = acf.get_account_qr()
+    alice.add_transport_from_qr(qr)
+
+    alice_provide_backup_future = alice._rpc.provide_backup.future(alice.id)
+    qr = alice._rpc.get_backup_qr(alice.id)
+
+    remote_eval("locals().setdefault('new_account', bob.manager.add_account())")
+    remote_eval(f"new_account._rpc.get_backup(new_account.id, {qr!r})")
+    alice_provide_backup_future()
+
+    assert alice.get_config("displayname") == remote_eval("new_account.get_config('displayname')")
+
+    first_transport_addr = alice.list_transports()[0]["addr"]
+    remote_eval(f"new_account.delete_transport({first_transport_addr!r})")
+
+
@pytest.mark.parametrize("replace_relay", [False, True], ids=["add", "replace"])
 def test_keyupdate_against_core_2_48_march_2026(acf, alice_and_remote_bob, replace_relay):
    """Test 2.48 Bob learns a relay change of Alice from a keyupdate, and is shown nothing."""
@@ -104,7 +129,6 @@ def test_keyupdate_against_core_2_48_march_2026(acf, alice_and_remote_bob, repla
    # an accepted chat alone is not enough, a message must have flowed.
    alice_chat = alice_contact_bob.create_chat()
    alice.set_config("keyupdate_debounce", "1")
-    old_addr = alice.get_config("configured_addr")
    alice_chat.send_text("hi")
    assert remote_eval("bob.wait_for_incoming_msg().get_snapshot().text") == "hi"
    before = bob_sees()
@@ -113,8 +137,9 @@ def test_keyupdate_against_core_2_48_march_2026(acf, alice_and_remote_bob, repla
    # and signature timestamps have one-second resolution:
    # without waiting, the re-signed key can tie with the copy Bob holds, keeping his.
    time.sleep(2)
+    old_addr = alice.list_transports()[0]["addr"]
    alice.add_transport_from_qr(acf.get_account_qr())
-    (new_addr,) = [t["addr"] for t in alice.list_transports() if t["addr"] != old_addr]
+    new_addr = alice.list_transports()[1]["addr"]
    if replace_relay:
        alice.delete_transport(old_addr)
    alice.bring_online()
@@ -50,8 +50,6 @@ SETUP_DATA = b"realtime-setup"


 def setup_realtime_webxdc(ac1, ac2, path_to_webxdc, wait=True):
-    assert ac1.get_config("webxdc_realtime_enabled") == "1"
-    assert ac2.get_config("webxdc_realtime_enabled") == "1"
    ac1_ac2_chat = ac1.create_chat(ac2)
    ac2.create_chat(ac1)

@@ -45,10 +45,8 @@ def test_add_second_address(acf) -> None:
    second_addr = account.list_transports()[1]["addr"]
    third_addr = account.list_transports()[2]["addr"]

-    assert account.get_config("configured_addr") == first_addr
    account.delete_transport(first_addr)
    assert len(account.list_transports()) == 2
-    assert account.get_config("configured_addr") != first_addr

    account.delete_transport(second_addr)
    assert len(account.list_transports()) == 1
@@ -187,9 +185,6 @@ def test_transport_synchronization(acf, log) -> None:
    wait_for_io_started(ac1)
    [transport1, transport3] = ac1.list_transports()

-    log.section("ac1 changes the sending transport")
-    ac1.set_config("configured_addr", transport3["addr"])
-
    log.section("ac1 removes the first transport")
    ac1.delete_transport(transport1["addr"])

@@ -197,7 +192,6 @@ def test_transport_synchronization(acf, log) -> None:
    wait_for_io_started(ac1_clone)
    [transport3] = ac1_clone.list_transports()
    assert transport3["addr"] == addr3
-    assert ac1_clone.get_config("configured_addr") == addr3

    ac2_chat = ac2.create_chat(ac1)
    ac2_chat.send_text("Hello!")
@@ -206,8 +200,8 @@ def test_transport_synchronization(acf, log) -> None:
    assert ac1_clone.wait_for_incoming_msg().get_snapshot().text == "Hello!"


-def test_transport_sync_new_as_primary(acf, log) -> None:
-    """Test that a transport promoted on one device is usable on other devices."""
+def test_receive_message_after_transport_sync(acf) -> None:
+    """Test that second device can receive messages after transport synchronization."""
    ac1, bob = acf.get_online_accounts(2)
    ac1_clone = ac1.clone()
    ac1_clone.bring_online()
@@ -221,12 +215,7 @@ def test_transport_sync_new_as_primary(acf, log) -> None:
    [transport1, transport2] = ac1_transports
    ac1_clone.wait_for_event(EventType.TRANSPORTS_MODIFIED)
    assert len(ac1_clone.list_transports()) == 2
-    assert ac1_clone.get_config("configured_addr") == transport1["addr"]

-    log.section("ac1 changes the primary transport")
-    ac1.set_config("configured_addr", transport2["addr"])
-
-    log.section("ac1_clone receives a message via the new transport")
    ac1_chat = ac1.create_chat(bob)
    ac1_chat.send_text("Hello!")
    bob_chat_id = bob.wait_for_incoming_msg_event().chat_id
@@ -236,22 +225,6 @@ def test_transport_sync_new_as_primary(acf, log) -> None:
    assert ac1_clone.wait_for_incoming_msg().get_snapshot().text == "hello back"


-def test_recognize_self_address(acf) -> None:
-    alice, bob = acf.get_online_accounts(2)
-
-    bob_chat = bob.create_chat(alice)
-
-    qr = acf.get_account_qr()
-    alice.add_transport_from_qr(qr)
-
-    new_alice_addr = alice.list_transports()[1]["addr"]
-    alice.set_config("configured_addr", new_alice_addr)
-
-    bob_chat.send_text("Hello!")
-    msg = alice.wait_for_incoming_msg().get_snapshot()
-    assert msg.chat == alice.create_chat(bob)
-
-
 def test_transport_limit(acf) -> None:
    """Test transports limit."""
    account = acf.get_online_account()
@@ -294,7 +267,6 @@ def test_message_info_imap_urls(acf) -> None:

    # Alice switches to another transport and removes the rest of the transports.
    new_alice_addr = alice.list_transports()[1]["addr"]
-    alice.set_config("configured_addr", new_alice_addr)
    removed_addrs = []
    for transport in alice.list_transports():
        if transport["addr"] != new_alice_addr:
@@ -326,7 +298,6 @@ def test_remove_primary_transport(acf, log) -> None:

    log.section("Alice removes the primary relay")
    alice.delete_transport(transport1["addr"])
-    assert alice.get_config("configured_addr") == transport2["addr"]
    alice.stop_io()
    alice.start_io()

@@ -369,7 +340,6 @@ def test_qr_works_after_removing_primary_transport(acf, log) -> None:
 def test_background_fetch_from_second_transport(acf, direct_imap, dc):
    alice, alice_chat, bob_chat = alice_with_two_transports_and_bob(acf)
    [transport1, transport2] = alice.list_transports()
-    assert alice.get_config("configured_addr") == transport1["addr"]

    alice.stop_io()
    bob_chat.send_text("hello")
@@ -647,9 +647,8 @@ def test_qr_scan_updates_new_relay_address(acf):
    bob.wait_for_securejoin_joiner_success()

    for ac in [alice, bob]:
-        old_addr = ac.get_config("configured_addr")
+        old_addr = ac.list_transports()[0]["addr"]
        ac.add_transport_from_qr(acf.get_account_qr())
-        ac.set_config("configured_addr", ac.list_transports()[1]["addr"])
        ac.delete_transport(old_addr)

    bob.secure_join(alice.get_qr_code())
@@ -100,7 +100,6 @@ def test_lowercase_address(acf) -> None:
    )
    assert account.is_configured()
    assert addr_upper != addr
-    assert account.get_config("configured_addr") == addr
    assert account.list_transports()[0]["addr"] == addr

    param = account.get_info()["used_transport_settings"]
@@ -168,7 +167,7 @@ def test_list_transports(acf) -> None:
 def test_account(acf) -> None:
    alice, bob = acf.get_online_accounts(2)

-    bob_addr = bob.get_config("configured_addr")
+    bob_addr = bob.list_transports()[0]["addr"]
    alice_contact_bob = alice.create_contact(bob, "Bob")
    alice_chat_bob = alice_contact_bob.create_chat()
    alice_chat_bob.send_text("Hello!")
@@ -331,7 +330,7 @@ def test_chat(acf) -> None:
 def test_contact(acf) -> None:
    alice, bob = acf.get_online_accounts(2)

-    bob_addr = bob.get_config("configured_addr")
+    bob_addr = bob.list_transports()[0]["addr"]
    alice_contact_bob = alice.create_contact(bob, "Bob")

    assert alice_contact_bob == alice.get_contact_by_id(alice_contact_bob.id)
@@ -1489,3 +1488,19 @@ def test_is_sending_finished(dc, acf) -> None:
    bob.wait_for_event(EventType.SMTP_MESSAGE_SENT)

    assert dc.is_sending_finished()
+
+
+def test_pseudo_transport_start_stop_io(acf):
+    """
+    Test that I/O can be started and stopped for pseudo transport.
+
+    Pseudo transport has no connection candidates,
+    so in the past this resulted in IMAP busy looping
+    and stop_io() failing to even cancel the loop sometimes.
+    This is a regression test for this bug.
+    """
+    for i in range(10):
+        alice = acf.get_unconfigured_account()
+        alice.add_pseudo_transport(f"alice{i}@example.net")
+        alice.start_io()
+        alice.stop_io()
@@ -1,6 +1,6 @@
 [package]
 name = "deltachat-rpc-server"
-version = "2.63.0"
+version = "2.66.0-dev"
 description = "DeltaChat JSON-RPC server"
 edition = "2024"
 license = "MPL-2.0"
@@ -15,5 +15,5 @@
  },
  "type": "module",
  "types": "index.d.ts",
-  "version": "2.63.0"
+  "version": "2.66.0-dev"
 }
@@ -30,9 +30,11 @@ ignore = [
    # <https://rustsec.org/advisories/RUSTSEC-2026-0049>
    # <https://rustsec.org/advisories/RUSTSEC-2026-0098>
    # <https://rustsec.org/advisories/RUSTSEC-2026-0099>
+    # <https://rustsec.org/advisories/RUSTSEC-2026-0382>
    "RUSTSEC-2026-0049",
    "RUSTSEC-2026-0098",
    "RUSTSEC-2026-0099",
+    "RUSTSEC-2026-0382",

    # Panic in CRL signature checks.
    # We do not check CRL and cannot update rustls-webpki 0.102.8 
@@ -54,6 +56,14 @@ ignore = [
    # We enable PQC for encryption rather than signatures.
    # <https://rustsec.org/advisories/RUSTSEC-2025-0144>
    "RUSTSEC-2025-0144",
+
+    # Timing side channels in crypto-bigint 0.5.5, fixed only in 0.7.6.
+    # rPGP 0.21 depends on elliptic-curve 0.13 and cx448 0.1,
+    # which require crypto-bigint^0.5.
+    # Delta by default uses only Ed25519 and X25519 (and RSA keys from old profiles)
+    # that do not use crypto-bigint.
+    # <https://rustsec.org/advisories/RUSTSEC-2026-0387>
+    "RUSTSEC-2026-0387",
 ]

 [bans]
@@ -98,6 +108,7 @@ skip = [
     { name = "thiserror", version = "1.0.69" },
     { name = "toml_datetime", version = "0.6.11" },
     { name = "wasi", version = "0.11.0+wasi-snapshot-preview1" },
+     { name = "webpki-roots", version = "0.26.8" },
     { name = "windows" },
     { name = "windows_aarch64_gnullvm" },
     { name = "windows_aarch64_msvc" },
@@ -127,6 +138,7 @@ allow = [
    "BSD-3-Clause",
    "BSL-1.0", # Boost Software License 1.0
    "CC0-1.0",
+    "CDLA-Permissive-2.0",
    "ISC",
    "MIT",
    "MPL-2.0",
@@ -471,6 +471,19 @@ CREATE TABLE smtp_success (
    FOREIGN KEY(transport_id) REFERENCES transports(id) ON DELETE CASCADE
 ) STRICT;

+-- Similar to smtp_success, but records failures.
+CREATE TABLE smtp_failure (
+    -- Sequentially increasing ID of the failure
+    -- Transport with the highest ID is to be used last.
+    id INTEGER PRIMARY KEY AUTOINCREMENT NOT NULL,
+
+    -- ID of the transport that was used to attempt sending a message.
+    transport_id INTEGER UNIQUE NOT NULL,
+
+    -- Delete `smtp_failure` rows when the transport is deleted.
+    FOREIGN KEY(transport_id) REFERENCES transports(id) ON DELETE CASCADE
+) STRICT;
+
 -- Table of "sync items" to be grouped into sync messages
 -- and sent to own devices.
 CREATE TABLE multi_device_sync (
@@ -710,6 +723,7 @@ CREATE TABLE imap (
 CREATE INDEX imap_folder ON imap(transport_id, folder);
 CREATE INDEX imap_rfc724_mid ON imap(transport_id, rfc724_mid);
 CREATE INDEX imap_only_rfc724_mid ON imap(rfc724_mid);
+CREATE INDEX imap_pending_deletions ON imap(transport_id, folder) WHERE target != folder;

 CREATE TABLE imap_markseen (
    id INTEGER PRIMARY KEY NOT NULL,
@@ -4,7 +4,7 @@ build-backend = "setuptools.build_meta"

 [project]
 name = "deltachat"
-version = "2.63.0"
+version = "2.66.0-dev"
 license = "MPL-2.0"
 description = "Python bindings for the Delta Chat Core library using CFFI against the Rust-implemented libdeltachat"
 readme = "README.rst"
@@ -370,12 +370,7 @@ class ACFactory:
        acname = ac._logid
        addr = f"{acname}@offline.org"
        lib.dc_add_pseudo_transport(ac._dc_context, as_dc_charpointer(addr))
-        ac.update_config(
-            {
-                "configured_addr": addr,
-                "displayname": acname,
-            },
-        )
+        ac.set_config("displayname", acname)
        self._preconfigure_key(ac)
        self._acsetup.init_logging(ac)
        assert ac.is_configured(), "Pseudo configured account should look like if it is configured"
@@ -51,7 +51,6 @@ class TestGroupStressTests:

        lp.sec("ac2: receiving system message about contact addition")
        sysmsg = ac2._evtracker.wait_next_incoming_message()
-        assert ac5.get_config("configured_addr") in sysmsg.text
        assert sysmsg.chat.num_contacts() == 4

        lp.sec("ac5: waiting for message about addition to the chat")
@@ -132,7 +132,7 @@ class TestOfflineContact:

    def test_create_self_contact(self, acfactory):
        ac1 = acfactory.get_pseudo_configured_account()
-        contact1 = ac1.create_contact(ac1.get_config("configured_addr"))
+        contact1 = ac1.create_contact(ac1.get_self_contact().addr)
        assert contact1.id == 1

    def test_get_contacts_and_delete(self, acfactory):
@@ -223,7 +223,7 @@ class TestOfflineChat:
        ac2 = acfactory.get_pseudo_configured_account()
        chat = ac1.create_group_chat(name="title1")
        contact = chat.add_contact(ac2)
-        assert contact.addr == ac2.get_config("configured_addr")
+        assert contact.addr == ac2.get_self_contact().addr
        assert contact.name == ac2.get_config("displayname")
        assert contact.account == ac1
        chat.remove_contact(ac2)
@@ -456,7 +456,7 @@ class TestOfflineChat:
        contacts = ac2.get_contacts()
        assert len(contacts) == 1
        contact2 = contacts[0]
-        assert contact2.addr == ac_contact.get_config("configured_addr")
+        assert contact2.addr == ac_contact.get_self_contact().addr
        chat2 = contact2.create_chat()
        messages = chat2.get_messages()
        assert len(messages) == 2 + E2EE_INFO_MSGS
@@ -552,7 +552,7 @@ class TestOfflineChat:
        contacts = ac2.get_contacts()
        assert len(contacts) == 1
        contact2 = contacts[0]
-        assert contact2.addr == ac_contact.get_config("configured_addr")
+        assert contact2.addr == ac_contact.get_self_contact().addr
        chat2 = contact2.create_chat()
        messages = chat2.get_messages()
        assert len(messages) == 2 + E2EE_INFO_MSGS
@@ -604,7 +604,7 @@ class TestOfflineChat:
        contacts = ac2.get_contacts()
        assert len(contacts) == 1
        contact2 = contacts[0]
-        assert contact2.addr == ac_contact.get_config("configured_addr")
+        assert contact2.addr == ac_contact.get_self_contact().addr
        chat2 = contact2.create_chat()
        messages = chat2.get_messages()
        assert len(messages) == 2 + E2EE_INFO_MSGS
@@ -621,7 +621,7 @@ class TestOfflineChat:
        contacts = ac2.get_contacts()
        assert len(contacts) == 1
        contact2 = contacts[0]
-        assert contact2.addr == ac_contact.get_config("configured_addr")
+        assert contact2.addr == ac_contact.get_self_contact().addr
        chat2 = contact2.create_chat()
        messages = chat2.get_messages()
        assert len(messages) == 2 + E2EE_INFO_MSGS
@@ -1 +1 @@
-2026-10-09
+2026-10-22
@@ -123,6 +123,45 @@ impl CallInfo {
        Ok(())
    }

+    /// Returns call state.
+    pub fn call_state(&self) -> CallState {
+        if self.is_incoming() {
+            if self.is_accepted() {
+                if self.is_ended() {
+                    CallState::Completed {
+                        duration: self.duration_seconds(),
+                    }
+                } else {
+                    CallState::Active
+                }
+            } else if self.is_canceled() {
+                // Call was explicitly canceled
+                // by the caller before we picked it up.
+                CallState::Missed
+            } else if self.is_ended() {
+                CallState::Declined
+            } else if self.is_stale() {
+                CallState::Missed
+            } else {
+                CallState::Alerting
+            }
+        } else if self.is_accepted() {
+            if self.is_ended() {
+                CallState::Completed {
+                    duration: self.duration_seconds(),
+                }
+            } else {
+                CallState::Active
+            }
+        } else if self.is_canceled() {
+            CallState::Canceled
+        } else if self.is_ended() || self.is_stale() {
+            CallState::Declined
+        } else {
+            CallState::Alerting
+        }
+    }
+
    /// Returns true if the call is accepted.
    pub fn is_accepted(&self) -> bool {
        self.msg.param.exists(CALL_ACCEPTED_TIMESTAMP)
@@ -508,10 +547,10 @@ impl Context {
        Ok(self.load_call_by_message(call))
    }

-    // Loads information about the call given the `Message`.
-    //
-    // If the `Message` is not a call message, returns `None`
-    fn load_call_by_message(&self, call: Message) -> Option<CallInfo> {
+    /// Loads information about the call given the `Message`.
+    ///
+    /// If the `Message` is not a call message, returns `None`
+    pub fn load_call_by_message(&self, call: Message) -> Option<CallInfo> {
        if call.viewtype != Viewtype::Call {
            // This can happen e.g. if a "call accepted"
            // or "call ended" message is received
@@ -581,42 +620,7 @@ pub async fn call_state(context: &Context, msg_id: MsgId) -> Result<CallState> {
        .load_call_by_id(msg_id)
        .await?
        .with_context(|| format!("{msg_id} is not a call message"))?;
-    let state = if call.is_incoming() {
-        if call.is_accepted() {
-            if call.is_ended() {
-                CallState::Completed {
-                    duration: call.duration_seconds(),
-                }
-            } else {
-                CallState::Active
-            }
-        } else if call.is_canceled() {
-            // Call was explicitly canceled
-            // by the caller before we picked it up.
-            CallState::Missed
-        } else if call.is_ended() {
-            CallState::Declined
-        } else if call.is_stale() {
-            CallState::Missed
-        } else {
-            CallState::Alerting
-        }
-    } else if call.is_accepted() {
-        if call.is_ended() {
-            CallState::Completed {
-                duration: call.duration_seconds(),
-            }
-        } else {
-            CallState::Active
-        }
-    } else if call.is_canceled() {
-        CallState::Canceled
-    } else if call.is_ended() || call.is_stale() {
-        CallState::Declined
-    } else {
-        CallState::Alerting
-    };
-    Ok(state)
+    Ok(call.call_state())
 }

 /// ICE server for JSON serialization.
@@ -2893,15 +2893,9 @@ async fn create_send_msg_jobs(context: &Context, msg: &mut Message) -> Result<Ve
    let (queued_msg, side_effects) = queued_msg_pair;

    if needs_encryption && !is_encrypted {
-        let addr = context.get_config(Config::ConfiguredAddr).await?;
-        let text = stock_str::unencrypted_email(
-            context,
-            addr.unwrap_or_default()
-                .split('@')
-                .nth(1)
-                .unwrap_or_default(),
-        )
-        .await;
+        let addr = context.get_primary_self_addr().await?;
+        let text =
+            stock_str::unencrypted_email(context, addr.split('@').nth(1).unwrap_or_default()).await;
        message::set_msg_failed(context, msg, &text).await?;
        add_info_msg_with_cmd(
            context,
@@ -4692,7 +4686,11 @@ pub(crate) async fn resend_msgs_ext(
                // Broadcast owners shouldn't see spinners on messages being auto-re-sent to new
                // subscribers (otherwise big channel owners will see spinners most of the time).
                if to_fingerprint.is_none() {
-                    message::update_msg_state(context, msg.id, MessageState::OutPending).await?;
+                    let sql = &context.sql;
+                    sql.transaction(|tx| {
+                        message::update_msg_state(tx, msg.id, MessageState::OutPending)
+                    })
+                    .await?;
                }
            }
            msg_state => bail!("Unexpected message state {msg_state}"),
@@ -4,7 +4,7 @@ use std::env;
 use std::path::Path;
 use std::str::FromStr;

-use anyhow::{Context as _, Result, bail, ensure};
+use anyhow::{Context as _, Result, ensure};
 use base64::Engine as _;
 use deltachat_contact_tools::{addr_cmp, sanitize_single_line};
 use serde::{Deserialize, Serialize};
@@ -197,11 +197,6 @@ pub enum Config {
    #[strum(props(default = "0"))]
    DeleteDeviceAfter,

-    /// Deprecated(2026-09).
-    ///
-    /// Use ConfiguredLoginParam and list_transports() instead.
-    ConfiguredAddr,
-
    /// Deprecated(2026-04).
    /// Use ConfiguredLoginParam and add_transport{from_qr}()/list_transports() instead.
    ///
@@ -442,10 +437,6 @@ pub enum Config {
    /// MsgId of webxdc map integration.
    WebxdcIntegration,

-    /// Enable webxdc realtime features.
-    #[strum(props(default = "1"))]
-    WebxdcRealtimeEnabled,
-
    /// Last device token stored on the chatmail server.
    ///
    /// If it has not changed, we do not store
@@ -752,34 +743,6 @@ impl Context {
                    .set_raw_config(key.as_ref(), value.map(|s| s.to_lowercase()).as_deref())
                    .await?;
            }
-            Config::ConfiguredAddr => {
-                let Some(addr) = value else {
-                    bail!("Cannot unset configured_addr");
-                };
-
-                self.sql
-                    .transaction(|transaction| {
-                        if transaction.query_row(
-                            "SELECT COUNT(*) FROM transports WHERE addr=?",
-                            (addr,),
-                            |row| {
-                                let res: i64 = row.get(0)?;
-                                Ok(res)
-                            },
-                        )? == 0
-                        {
-                            bail!("Address does not belong to any transport.");
-                        }
-                        transaction.execute(
-                            "INSERT OR REPLACE INTO config (keyname, value) VALUES ('configured_addr', ?)",
-                            (addr,),
-                        )?;
-
-                        Ok(())
-                    })
-                    .await?;
-                self.sql.uncache_raw_config("configured_addr").await;
-            }
            _ => {
                self.sql.set_raw_config(key.as_ref(), value).await?;
            }
@@ -854,18 +817,6 @@ impl Context {
    /// Determine whether the specified addr maps to the/a self addr.
    /// Returns `false` if no addresses are configured.
    pub(crate) async fn is_self_addr(&self, addr: &str) -> Result<bool> {
-        // Employ the config cache to optimize for `ConfiguredAddr` passed.
-        if !addr.is_empty()
-            && addr_cmp(
-                addr,
-                &self
-                    .get_config(Config::ConfiguredAddr)
-                    .await?
-                    .unwrap_or_default(),
-            )
-        {
-            return Ok(true);
-        }
        Ok(self
            .get_self_addrs()
            .await?
@@ -873,20 +824,6 @@ impl Context {
            .any(|a| addr_cmp(addr, a)))
    }

-    /// Sets `primary_new` as the address used for sending.
-    ///
-    /// This should only be used by test code and during configure.
-    #[cfg(test)] // AEAP is disabled, but there are still tests for it
-    pub(crate) async fn set_primary_self_addr(&self, primary_new: &str) -> Result<()> {
-        self.quota.write().await.clear();
-
-        self.sql
-            .set_raw_config(Config::ConfiguredAddr.as_ref(), Some(primary_new))
-            .await?;
-        self.emit_event(EventType::ConnectivityChanged);
-        Ok(())
-    }
-
    /// Returns all self addresses, newest first.
    pub(crate) async fn get_self_addrs(&self) -> Result<Vec<String>> {
        let query_only = true;
@@ -895,10 +832,10 @@ impl Context {
            .await
    }

-    /// Returns the address of the transport used for sending.
-    /// Returns an error if no self addr is configured.
+    /// Returns address of the first transport.
    pub async fn get_primary_self_addr(&self) -> Result<String> {
-        self.get_config(Config::ConfiguredAddr)
+        self.sql
+            .query_get_value("SELECT addr FROM transports ORDER BY id LIMIT 1", ())
            .await?
            .context("No self addr configured")
    }
@@ -37,8 +37,8 @@ use crate::sync::Sync::Nosync;
 use crate::tools::time;
 use crate::transport::{
    ConfiguredCertificateChecks, ConfiguredLoginParam, ConfiguredServerLoginParam,
-    ConnectionCandidate, delete_transport_row, maybe_update_sending_transport,
-    purge_transport_caches, send_sync_transports, transport_addrs,
+    ConnectionCandidate, delete_transport_row, purge_transport_caches, send_sync_transports,
+    transport_addrs, update_configured_addr,
 };
 use crate::{EventType, autorelay, stock_str};

@@ -275,7 +275,7 @@ impl Context {
    /// another one is chosen automatically.
    pub async fn delete_transport(&self, addr: &str) -> Result<()> {
        let now = time();
-        let (removed_transport_id, reelected) = self
+        let removed_transport_id = self
            .sql
            .transaction(|transaction| {
                if transport_addrs(transaction)?.len() <= 1 {
@@ -294,14 +294,10 @@ impl Context {
                let remove_timestamp = std::cmp::max(now, add_timestamp);
                let transport_id = delete_transport_row(transaction, addr, remove_timestamp)?
                    .context("Transport disappeared")?;
-                let reelected = maybe_update_sending_transport(transaction)?;
-                Ok((transport_id, reelected))
+                update_configured_addr(transaction)?;
+                Ok(transport_id)
            })
            .await?;
-        if let Some(new_addr) = reelected {
-            info!(self, "Using transport {new_addr:?} for sending now.");
-            self.sql.uncache_raw_config("configured_addr").await;
-        }
        send_sync_transports(self).await?;
        purge_transport_caches(self, removed_transport_id).await;
        // Restarting all IO also stops the removed transport's IMAP loop.
@@ -513,6 +509,8 @@ pub(crate) async fn configure(
        let smtp_password = configured_param.smtp_password.clone();
        let smtp_addr = configured_param.addr.clone();

+        let transport_id = 0;
+
        let proxy_config2 = proxy_config.clone();
        let smtp_config_task = task::spawn(async move {
            let mut smtp = Smtp::new();
@@ -522,6 +520,7 @@ pub(crate) async fn configure(
                &smtp_password,
                &proxy_config2,
                &smtp_addr,
+                transport_id,
                strict_tls,
            )
            .await?;
@@ -533,7 +532,6 @@ pub(crate) async fn configure(

        // Configure IMAP

-        let transport_id = 0;
        let (_s, r) = async_channel::bounded(1);
        let mut imap = Imap::new(ctx, transport_id, configured_param.clone(), r).await?;
        let imap_session = match imap.connect(ctx).await {
@@ -799,8 +797,6 @@ mod tests {
        let t = &tcm.unconfigured().await;

        add_pseudo_transport(t, "primary@example.org").await?;
-        t.set_config(Config::ConfiguredAddr, Some("primary@example.org"))
-            .await?;
        assert_eq!(t.count_transports().await?, 1);
        t.check_relay_limit().await?;

@@ -372,7 +372,11 @@ pub(crate) async fn import_public_key(
        .await?
    {
        let old_public_key = SignedPublicKey::from_slice(&public_key_bytes)?;
-        merged_public_key = merge_openpgp_certificates(public_key.clone(), old_public_key)
+
+        // Order of merge_openpgp_certificates() arguments is important.
+        // Second argument is the new key, it is preferred in case of ties,
+        // i.e. same signature timestamps.
+        merged_public_key = merge_openpgp_certificates(old_public_key, public_key.clone())
            .context("Failed to merge public keys")?;
        &merged_public_key
    } else {
@@ -718,9 +722,9 @@ impl Contact {
                    .await?
                    .unwrap_or_default();
                contact.addr = context
-                    .get_config(Config::ConfiguredAddr)
-                    .await?
-                    .unwrap_or_default();
+                    .get_primary_self_addr()
+                    .await
+                    .context("Cannot get address for self-contact")?;
                if let Some(self_fp) = self_fingerprint_opt(context).await? {
                    contact.fingerprint = Some(self_fp.to_string());
                }
@@ -1421,10 +1425,6 @@ WHERE addr=?
        );

        let contact = Contact::get_by_id(context, contact_id).await?;
-        let addr = context
-            .get_config(Config::ConfiguredAddr)
-            .await?
-            .unwrap_or_default();

        let Some(fingerprint_other) = contact.fingerprint() else {
            return Ok(stock_str::encr_none(context));
@@ -1444,37 +1444,15 @@ WHERE addr=?
            .await?
            .dc_fingerprint()
            .human_readable();
-        if addr < contact.addr {
-            cat_fingerprint(
-                &mut ret,
-                &stock_str::self_msg(context),
-                &addr,
-                &fingerprint_self,
-            );
-            cat_fingerprint(
-                &mut ret,
-                contact.get_display_name(),
-                &contact.addr,
-                &fingerprint_other,
-            );
+        if fingerprint_self < fingerprint_other {
+            cat_fingerprint(&mut ret, &stock_str::self_msg(context), &fingerprint_self);
+            cat_fingerprint(&mut ret, contact.get_display_name(), &fingerprint_other);
        } else {
-            cat_fingerprint(
-                &mut ret,
-                contact.get_display_name(),
-                &contact.addr,
-                &fingerprint_other,
-            );
-            cat_fingerprint(
-                &mut ret,
-                &stock_str::self_msg(context),
-                &addr,
-                &fingerprint_self,
-            );
+            cat_fingerprint(&mut ret, contact.get_display_name(), &fingerprint_other);
+            cat_fingerprint(&mut ret, &stock_str::self_msg(context), &fingerprint_self);
        }

-        if let Some(public_key) = contact.public_key(context).await?
-            && let Some(relay_addrs) = addresses_from_public_key(&public_key)
-        {
+        if let Some(relay_addrs) = contact.relay_addresses(context).await? {
            ret += "\n\nRelays:";
            for relay in &relay_addrs {
                ret += "\n";
@@ -1604,6 +1582,17 @@ WHERE addr=?
        }
    }

+    /// Returns a list of relay addresses for the contact if it is distributed in the public key.
+    pub(crate) async fn relay_addresses(&self, context: &Context) -> Result<Option<Vec<String>>> {
+        if let Some(public_key) = self.public_key(context).await?
+            && let Some(relay_addrs) = addresses_from_public_key(&public_key)
+        {
+            Ok(Some(relay_addrs))
+        } else {
+            Ok(None)
+        }
+    }
+
    /// Get name authorized by the contact.
    pub fn get_authname(&self) -> &str {
        &self.authname
@@ -1968,8 +1957,8 @@ pub(crate) async fn update_last_seen(
    Ok(())
 }

-fn cat_fingerprint(ret: &mut String, name: &str, addr: &str, fingerprint: &str) {
-    *ret += &format!("\n\n{name} ({addr}):\n{fingerprint}");
+fn cat_fingerprint(ret: &mut String, name: &str, fingerprint: &str) {
+    *ret += &format!("\n\n{name}:\n{fingerprint}");
 }

 fn split_address_book(book: &str) -> Vec<(&str, &str)> {
@@ -3,6 +3,7 @@ use deltachat_contact_tools::{addr_cmp, may_be_valid_addr};
 use super::*;
 use crate::chat::{Chat, get_chat_contacts, send_text_msg};
 use crate::chatlist::Chatlist;
+use crate::key::secret_key_to_public_key;
 use crate::receive_imf::receive_imf;
 use crate::securejoin::get_securejoin_qr;
 use crate::test_utils::{self, TestContext, TestContextManager, TimeShiftFalsePositiveNote, sync};
@@ -887,11 +888,11 @@ async fn test_contact_get_encrinfo() -> Result<()> {
        "Messages are end-to-end encrypted.
 Fingerprints:

-Me (alice@example.org):
+Me:
 2E6F A2CB 23B5 32D7 2863
 4B58 64B0 8F61 A9ED 9443

-bob@example.net (bob@example.net):
+bob@example.net:
 CCCB 5AA9 F6E1 141C 9431
 65F1 DB18 B18C BCF7 0487

@@ -908,11 +909,11 @@ bob@example.net"
        "No encryption.
 Fingerprints:

-Me (alice@example.org):
+Me:
 2E6F A2CB 23B5 32D7 2863
 4B58 64B0 8F61 A9ED 9443

-bob@example.net (bob@example.net):
+bob@example.net:
 CCCB 5AA9 F6E1 141C 9431
 65F1 DB18 B18C BCF7 0487"
    );
@@ -1252,7 +1253,7 @@ async fn test_make_n_import_vcard() -> Result<()> {
    tokio::fs::write(&avatar_path, avatar_bytes).await?;
    bob.set_config(Config::Selfavatar, Some(avatar_path.to_str().unwrap()))
        .await?;
-    let bob_addr = bob.get_config(Config::ConfiguredAddr).await?.unwrap();
+    let bob_addr = bob.get_primary_self_addr().await?;
    let bob_biography = bob.get_config(Config::Selfstatus).await?.unwrap();
    let chat = bob.create_chat(alice).await;
    let sent_msg = bob.send_text(chat.id, "moin").await;
@@ -1348,7 +1349,7 @@ async fn test_make_n_import_vcard() -> Result<()> {
 async fn test_import_vcard_key_change() -> Result<()> {
    let alice = &TestContext::new_alice().await;
    let bob = &TestContext::new_bob().await;
-    let bob_addr = &bob.get_config(Config::ConfiguredAddr).await?.unwrap();
+    let bob_addr = &bob.get_primary_self_addr().await?;
    bob.set_config(Config::Displayname, Some("Bob")).await?;
    let vcard = make_vcard(bob, &[ContactId::SELF]).await?;
    alice.evtracker.clear_events();
@@ -1560,3 +1561,44 @@ async fn test_same_avatar_no_changed_event() -> Result<()> {

    Ok(())
 }
+
+/// Tests that relay list from imported key is preferred if the signature
+/// has the same timestamp as already imported key.
+/// If they key is signed twice with different relay list at the same second,
+/// we want to use the relay list from the message that arrives last
+/// so the newest relay list is used unless the messages are reordered.
+#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+async fn test_import_public_key_tiebreak() -> Result<()> {
+    let mut tcm = TestContextManager::new();
+    let alice = &tcm.alice().await;
+    let bob = &tcm.bob().await;
+
+    let contact = bob.add_or_lookup_contact(alice).await;
+
+    let secret_key = test_utils::alice_keypair();
+    let timestamp = pgp::types::Timestamp::now();
+
+    let addr = "alice@example.net";
+    let relays1 = "alice@example.net,alice@example.org";
+    let relays2 = "alice@example.net,alice@example.com";
+    let relays1_vec: Vec<String> = relays1.split(',').map(String::from).collect();
+    let relays2_vec: Vec<String> = relays2.split(',').map(String::from).collect();
+
+    let public_key1 =
+        secret_key_to_public_key(secret_key.clone(), timestamp.as_secs(), addr, relays1)?;
+    let public_key2 = secret_key_to_public_key(secret_key, timestamp.as_secs(), addr, relays2)?;
+
+    import_public_key(bob, &public_key1).await?;
+    assert_eq!(contact.relay_addresses(bob).await?.unwrap(), relays1_vec);
+
+    import_public_key(bob, &public_key2).await?;
+    assert_eq!(contact.relay_addresses(bob).await?.unwrap(), relays2_vec);
+
+    import_public_key(bob, &public_key1).await?;
+    assert_eq!(contact.relay_addresses(bob).await?.unwrap(), relays1_vec);
+
+    import_public_key(bob, &public_key2).await?;
+    assert_eq!(contact.relay_addresses(bob).await?.unwrap(), relays2_vec);
+
+    Ok(())
+}
@@ -949,12 +949,6 @@ impl Context {
            "gossip_period",
            self.get_config_int(Config::GossipPeriod).await?.to_string(),
        );
-        res.insert(
-            "webxdc_realtime_enabled",
-            self.get_config_bool(Config::WebxdcRealtimeEnabled)
-                .await?
-                .to_string(),
-        );
        res.insert(
            "donation_request_next_check",
            self.get_config_i64(Config::DonationRequestNextCheck)
@@ -279,65 +279,20 @@ pub(crate) async fn stock_ephemeral_timer_changed(
 }

 impl MsgId {
-    /// Returns ephemeral message timer value for the message.
-    pub(crate) async fn ephemeral_timer(self, context: &Context) -> Result<Timer> {
-        let res = match context
-            .sql
-            .query_get_value("SELECT ephemeral_timer FROM msgs WHERE id=?", (self,))
-            .await?
-        {
-            None => Timer::Disabled,
-            Some(duration) => Timer::from_u32(duration),
-        };
-        Ok(res)
-    }
-
    /// Starts ephemeral message timer for the message if it is not started yet.
-    pub(crate) async fn start_ephemeral_timer(self, context: &Context) -> Result<()> {
-        if let Timer::Enabled { duration } = self.ephemeral_timer(context).await? {
-            let ephemeral_timestamp = time().saturating_add(duration.get().into());
-
-            context
-                .sql
-                .execute(
-                    "UPDATE msgs SET ephemeral_timestamp = ? \
-                WHERE (ephemeral_timestamp == 0 OR ephemeral_timestamp > ?) \
-                AND id = ?",
-                    (ephemeral_timestamp, ephemeral_timestamp, self),
-                )
-                .await?;
-            context.scheduler.interrupt_ephemeral_task().await;
-        }
-        Ok(())
+    ///
+    /// Returns whether the timer was started.
+    pub(crate) fn start_ephemeral_timer(self, tx: &rusqlite::Transaction) -> Result<bool> {
+        let updated = tx.execute(
+            "UPDATE msgs SET ephemeral_timestamp = ?1 + ephemeral_timer
+             WHERE (ephemeral_timestamp == 0 OR ephemeral_timestamp > ?1 + ephemeral_timer)
+             AND ephemeral_timer > 0 AND id=?2",
+            (time(), self),
+        )?;
+        Ok(updated > 0)
    }
 }

-pub(crate) async fn start_ephemeral_timers_msgids(
-    context: &Context,
-    msg_ids: &[MsgId],
-) -> Result<()> {
-    let now = time();
-    let should_interrupt =
-    context
-        .sql
-        .transaction(move |transaction| {
-            let mut should_interrupt = false;
-            let mut stmt =
-                transaction.prepare(
-                    "UPDATE msgs SET ephemeral_timestamp = ?1 + ephemeral_timer
-                     WHERE (ephemeral_timestamp == 0 OR ephemeral_timestamp > ?1 + ephemeral_timer) AND ephemeral_timer > 0
-                     AND id=?2")?;
-            for msg_id in msg_ids {
-                should_interrupt |= stmt.execute((now, msg_id))? > 0;
-            }
-            Ok(should_interrupt)
-        }).await?;
-    if should_interrupt {
-        context.scheduler.interrupt_ephemeral_task().await;
-    }
-    Ok(())
-}
-
 /// Starts ephemeral timer for all messages in the chat.
 ///
 /// This should be called when chat is marked as noticed.
@@ -379,7 +334,7 @@ async fn select_expired_messages(
 SELECT id, chat_id, type, pinned, location_id
 FROM msgs
 WHERE
-  ephemeral_timestamp != 0
+  ephemeral_timestamp > 0
  AND ephemeral_timestamp <= ?
  AND chat_id != ?
 "#,
@@ -560,6 +515,14 @@ async fn next_delete_device_after_timestamp(context: &Context) -> Result<Option<
    }
 }

+/// `> 0` rather than `!= 0`, so that SQLite uses `msgs_index8`.
+const NEXT_EPHEMERAL_TIMESTAMP: &str = "
+    SELECT min(ephemeral_timestamp)
+    FROM msgs
+    WHERE ephemeral_timestamp > 0
+      AND chat_id != ?
+    HAVING count(*) > 0";
+
 /// Calculates next timestamp when expiration of some message will happen.
 ///
 /// Expiration can happen either because user has set `delete_device_after` setting or because the
@@ -568,13 +531,7 @@ async fn next_expiration_timestamp(context: &Context) -> Option<i64> {
    let ephemeral_timestamp: Option<i64> = match context
        .sql
        .query_get_value(
-            r#"
-            SELECT min(ephemeral_timestamp)
-            FROM msgs
-            WHERE ephemeral_timestamp != 0
-              AND chat_id != ?
-            HAVING count(*) > 0
-            "#,
+            NEXT_EPHEMERAL_TIMESTAMP,
            (ChatId::TRASH,), // Trash contains already deleted messages, skip them
        )
        .await
@@ -661,6 +618,60 @@ pub(crate) async fn ephemeral_loop(context: &Context, interrupt_receiver: Receiv
    }
 }

+/// Driven by `imap`: with `bcc_self` off and `force_encryption` on core deletes downloaded
+/// messages from the server and their `imap` rows with them, leaving rows only for messages
+/// it does not download.
+const MARK_DOWNLOADED_FOR_DELETION: &str = "
+    UPDATE imap
+    SET target=''
+    WHERE transport_id=?1 AND target!=''
+    AND (EXISTS (
+            SELECT 1 FROM msgs
+            WHERE rfc724_mid=imap.rfc724_mid
+              AND id>9
+              AND ((ephemeral_timestamp!=0 AND ephemeral_timestamp<=?2) OR download_state=?3))
+        OR EXISTS (
+            SELECT 1 FROM msgs
+            WHERE pre_rfc724_mid=imap.rfc724_mid
+              AND pre_rfc724_mid!=''
+              AND id>9))";
+
+/// Driven by `imap` like [`MARK_DOWNLOADED_FOR_DELETION`]: with `bcc_self` and
+/// `force_encryption` off core deletes only encrypted and expired messages from the server,
+/// so the rows of other messages remain.
+const MARK_ENCRYPTED_FOR_DELETION: &str = "
+    UPDATE imap
+    SET target=''
+    WHERE transport_id=?1 AND target!=''
+    AND (EXISTS (
+            SELECT 1 FROM msgs
+            WHERE rfc724_mid=imap.rfc724_mid
+              AND id>9
+              AND ((ephemeral_timestamp!=0 AND ephemeral_timestamp<=?2) OR
+                   ((param GLOB '*\nc=1*' OR param GLOB 'c=1*') AND download_state=?3)))
+        OR EXISTS (
+            SELECT 1 FROM msgs
+            WHERE pre_rfc724_mid=imap.rfc724_mid
+              AND pre_rfc724_mid!=''
+              AND id>9
+              AND ((ephemeral_timestamp!=0 AND ephemeral_timestamp<=?2) OR
+                   (param GLOB '*\nc=1*' OR param GLOB 'c=1*'))))";
+
+/// Driven by `msgs_index8`: in multi-device mode core leaves downloaded messages on the server,
+/// so the `imap` table keeps a row for every message core has not deleted there.
+const MARK_EXPIRED_FOR_DELETION: &str = "
+    UPDATE imap
+    SET target=''
+    WHERE transport_id=?1 AND target!=''
+    AND rfc724_mid IN (
+        SELECT rfc724_mid FROM msgs
+        WHERE ephemeral_timestamp>0 AND ephemeral_timestamp<=?2 AND id>9
+        UNION
+        SELECT pre_rfc724_mid FROM msgs
+        WHERE pre_rfc724_mid!=''
+            AND ephemeral_timestamp>0 AND ephemeral_timestamp<=?2 AND id>9
+    )";
+
 /// Schedules expired IMAP messages for deletion on the server.
 ///
 /// Also see [`delete_expired_messages`],
@@ -684,18 +695,7 @@ pub(crate) async fn delete_expired_imap_messages(
        context
            .sql
            .execute(
-                "UPDATE imap
-                SET target=''
-                WHERE transport_id=?1
-                AND rfc724_mid IN (
-                    SELECT rfc724_mid FROM msgs
-                    WHERE ((ephemeral_timestamp!=0 AND ephemeral_timestamp<=?2) OR download_state=?3)
-                        AND id>9
-                    UNION
-                    SELECT pre_rfc724_mid FROM msgs
-                    WHERE pre_rfc724_mid!=''
-                        AND id>9
-                )",
+                MARK_DOWNLOADED_FOR_DELETION,
                (transport_id, now, DownloadState::Done),
            )
            .await?;
@@ -705,20 +705,7 @@ pub(crate) async fn delete_expired_imap_messages(
        // Only delete expired ephemeral messages.
        context
            .sql
-            .execute(
-                "UPDATE imap
-                SET target=''
-                WHERE transport_id=?1
-                AND rfc724_mid IN (
-                    SELECT rfc724_mid FROM msgs
-                    WHERE ephemeral_timestamp!=0 AND ephemeral_timestamp<=?2 AND id>9
-                    UNION
-                    SELECT pre_rfc724_mid FROM msgs
-                    WHERE pre_rfc724_mid!=''
-                        AND ephemeral_timestamp!=0 AND ephemeral_timestamp<=?2 AND id>9
-                )",
-                (transport_id, now),
-            )
+            .execute(MARK_EXPIRED_FOR_DELETION, (transport_id, now))
            .await?;
    } else {
        // Single device, but unencrypted messages are allowed.
@@ -726,21 +713,7 @@ pub(crate) async fn delete_expired_imap_messages(
        context
            .sql
            .execute(
-                "UPDATE imap
-                 SET target=''
-                 WHERE transport_id=?1
-                 AND rfc724_mid IN (
-                    SELECT rfc724_mid FROM msgs
-                    WHERE id>9
-                      AND ((ephemeral_timestamp!=0 AND ephemeral_timestamp<=?2) OR
-                           ((param GLOB '*\nc=1*' OR param GLOB 'c=1*') AND download_state=?3))
-                    UNION
-                    SELECT pre_rfc724_mid FROM msgs
-                    WHERE pre_rfc724_mid!=''
-                      AND id>9
-                      AND ((ephemeral_timestamp!=0 AND ephemeral_timestamp<=?2) OR
-                           (param GLOB '*\nc=1*' OR param GLOB 'c=1*'))
-                )",
+                MARK_ENCRYPTED_FOR_DELETION,
                (transport_id, now, DownloadState::Done),
            )
            .await?;
@@ -576,6 +576,31 @@ async fn test_delete_expired_imap_messages() -> Result<()> {
    Ok(())
 }

+#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+async fn test_expiration_queries_do_not_scan_msgs() -> Result<()> {
+    let t = TestContext::new_alice().await;
+    let mut scans = Vec::new();
+    for (name, query) in [
+        ("NEXT_EPHEMERAL_TIMESTAMP", NEXT_EPHEMERAL_TIMESTAMP),
+        ("MARK_DOWNLOADED_FOR_DELETION", MARK_DOWNLOADED_FOR_DELETION),
+        ("MARK_EXPIRED_FOR_DELETION", MARK_EXPIRED_FOR_DELETION),
+        ("MARK_ENCRYPTED_FOR_DELETION", MARK_ENCRYPTED_FOR_DELETION),
+    ] {
+        for step in t.query_plan(query).await? {
+            // These statements run after every IMAP fetch or sent message. `SCAN msgs` reads
+            // the whole table, and so does a rowid range from `id>9`, which SQLite plans as
+            // `SEARCH msgs USING INTEGER PRIMARY KEY (rowid>?)`. Index lookups and ranges pass.
+            if step.starts_with("SCAN msgs")
+                || step.ends_with("msgs USING INTEGER PRIMARY KEY (rowid>?)")
+            {
+                scans.push(format!("{name}: {step}"));
+            }
+        }
+    }
+    assert!(scans.is_empty(), "{scans:#?}");
+    Ok(())
+}
+
 // Regression test for a bug in the timer rollback protection.
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn test_ephemeral_timer_references() -> Result<()> {
@@ -16,8 +16,7 @@ use std::{
 use anyhow::{Context as _, Result, bail, ensure, format_err};
 use async_channel::{self, Receiver, Sender};
 use async_imap::types::{Fetch, Flag, UnsolicitedResponse};
-use futures::{FutureExt as _, TryStreamExt};
-use futures_lite::FutureExt;
+use futures::TryStreamExt as _;
 use ratelimit::Ratelimit;
 use tokio_util::sync::CancellationToken;
 use url::Url;
@@ -63,6 +62,20 @@ const RFC724MID_UID: &str = "(UID BODY.PEEK[HEADER.FIELDS (\
                             )])";
 const BODY_FULL: &str = "(FLAGS BODY.PEEK[])";

+const PENDING_DELETIONS: &str = "
+    SELECT id, uid, target FROM imap
+    WHERE folder = ?
+    AND transport_id = ?
+    AND target != folder
+    ORDER BY target, uid";
+
+/// `CROSS JOIN` loops over the few `imap_markseen` rows, not over the transport's `imap` rows.
+const PENDING_SEEN_FLAGS: &str = "
+    SELECT imap.id, uid, folder FROM imap_markseen CROSS JOIN imap
+    WHERE imap.id = imap_markseen.id
+    AND imap.transport_id=?
+    AND target = folder";
+
 #[derive(Debug)]
 pub(crate) struct Imap {
    /// ID of the transport configuration in the `transports` table.
@@ -274,17 +287,27 @@ impl Imap {
                "IMAP got rate limited, waiting for {} until can connect.",
                duration_to_str(ratelimit_duration),
            );
-            let interrupted = async {
-                tokio::time::sleep(ratelimit_duration).await;
-                false
-            }
-            .race(self.idle_interrupt_receiver.recv().map(|_| true))
-            .await;
-            if interrupted {
-                info!(
-                    context,
-                    "Connecting to IMAP without waiting for ratelimit due to interrupt."
-                );
+            match tokio::time::timeout(ratelimit_duration, self.idle_interrupt_receiver.recv())
+                .await
+            {
+                Ok(Ok(())) => {
+                    info!(
+                        context,
+                        "Connecting to IMAP without waiting for ratelimit due to interrupt."
+                    );
+                }
+                Ok(Err(async_channel::RecvError)) => {
+                    // If we get a RecvError, then this is likely because
+                    // the scheduler dropped the sender as it is stopping I/O.
+                    // Returning an error right away would make inbox_loop() call prepare() again.
+                    // Sleeping gives the executor a chance to cancel the loop;
+                    // the exact duration does not matter.
+                    tokio::time::sleep(Duration::from_secs(60)).await;
+                    bail!("Not connecting to IMAP because interrupt channel is closed");
+                }
+                Err(_) => {
+                    // Rate limit duration has passed.
+                }
            }
        }

@@ -301,6 +324,11 @@ impl Imap {
        self.conn_backoff_ms = max(BACKOFF_MIN_MS, self.conn_backoff_ms);

        let login_params = prioritize_server_login_params(&context.sql, &self.lp, "imap").await?;
+        if login_params.is_empty() {
+            // Count one connection attempt so we don't busy loop.
+            self.ratelimit.send();
+        }
+
        let mut first_connection_error = None;
        let mut first_login_error = None;
        'candidate: for lp in login_params {
@@ -453,8 +481,7 @@ impl Imap {
            context.scheduler.interrupt_ephemeral_task().await;
        }

-        // Mark expired messages for deletion. Note that `delete_expired_imap_messages` is
-        // not well optimized and should not be called before fetching.
+        // Mark messages for deletion on the server.
        delete_expired_imap_messages(context, session.transport_id())
            .await
            .context("delete_expired_imap_messages")?;
@@ -854,20 +881,12 @@ impl Session {
        let transport_id = self.transport_id();
        let rows = context
            .sql
-            .query_map_vec(
-                "SELECT id, uid, target FROM imap
-                 WHERE folder = ?
-                 AND transport_id = ?
-                 AND target != folder
-                 ORDER BY target, uid",
-                (folder, transport_id),
-                |row| {
-                    let rowid: i64 = row.get(0)?;
-                    let uid: u32 = row.get(1)?;
-                    let target: String = row.get(2)?;
-                    Ok((rowid, uid, target))
-                },
-            )
+            .query_map_vec(PENDING_DELETIONS, (folder, transport_id), |row| {
+                let rowid: i64 = row.get(0)?;
+                let uid: u32 = row.get(1)?;
+                let target: String = row.get(2)?;
+                Ok((rowid, uid, target))
+            })
            .await?;

        for (target, rowid_set, uid_set) in UidGrouper::from(rows) {
@@ -916,19 +935,12 @@ impl Session {
        let transport_id = self.transport_id();
        let mut rows = context
            .sql
-            .query_map_vec(
-                "SELECT imap.id, uid, folder FROM imap, imap_markseen
-                 WHERE imap.id = imap_markseen.id
-                 AND imap.transport_id=?
-                 AND target = folder",
-                (transport_id,),
-                |row| {
-                    let rowid: i64 = row.get(0)?;
-                    let uid: u32 = row.get(1)?;
-                    let folder: String = row.get(2)?;
-                    Ok((rowid, uid, folder))
-                },
-            )
+            .query_map_vec(PENDING_SEEN_FLAGS, (transport_id,), |row| {
+                let rowid: i64 = row.get(0)?;
+                let uid: u32 = row.get(1)?;
+                let folder: String = row.get(2)?;
+                Ok((rowid, uid, folder))
+            })
            .await?;

        // Number of SQL results is expected to be low as
@@ -1579,19 +1591,24 @@ pub(crate) async fn prefetch_should_download(
 /// Schedule marking the message as Seen on IMAP by adding all known IMAP messages corresponding to
 /// the given Message-ID to `imap_markseen` table.
 pub(crate) async fn markseen_on_imap_table(context: &Context, message_id: &str) -> Result<()> {
-    context
-        .sql
-        .execute(
-            "INSERT OR IGNORE INTO imap_markseen (id)
-             SELECT id FROM imap WHERE rfc724_mid=?",
-            (message_id,),
-        )
+    let sql = &context.sql;
+    sql.transaction(|tx| insert_imap_markseen(tx, message_id))
        .await?;
    context.scheduler.interrupt_inbox().await;

    Ok(())
 }

+/// Like [`markseen_on_imap_table`], but leaves interrupting the inbox loop to the caller.
+pub(crate) fn insert_imap_markseen(tx: &rusqlite::Transaction, message_id: &str) -> Result<()> {
+    tx.execute(
+        "INSERT OR IGNORE INTO imap_markseen (id)
+         SELECT id FROM imap WHERE rfc724_mid=?",
+        (message_id,),
+    )?;
+    Ok(())
+}
+
 /// uid_next is the next unique identifier value from the last time we fetched a folder
 /// See <https://tools.ietf.org/html/rfc3501#section-2.3.1.1>
 /// This function is used to update our uid_next after fetching messages.
@@ -116,3 +116,28 @@ fn test_uid_grouper() {
        vec![("INBOX".to_string(), vec![1, 2, 3], "2:3".to_string())]
    );
 }
+
+#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+async fn test_loop_queries_do_not_scan_imap() -> Result<()> {
+    let t = TestContext::new_alice().await;
+    let mut scans = Vec::new();
+    for (name, query) in [
+        ("PENDING_DELETIONS", PENDING_DELETIONS),
+        ("PENDING_SEEN_FLAGS", PENDING_SEEN_FLAGS),
+    ] {
+        for step in t.query_plan(query).await? {
+            // A step on the `imap` table (not `imap_markseen`) may only look up single rows
+            // by rowid or read the partial index of rows pending deletion. With any other index
+            // SQLite walks at least every `imap` row of the transport.
+            let reads_imap = step.contains(" imap ") || step.ends_with(" imap");
+            if reads_imap
+                && !step.contains("USING INTEGER PRIMARY KEY (rowid=?)")
+                && !step.contains("USING INDEX imap_pending_deletions ")
+            {
+                scans.push(format!("{name}: {step}"));
+            }
+        }
+    }
+    assert!(scans.is_empty(), "{scans:#?}");
+    Ok(())
+}
@@ -961,10 +961,6 @@ mod tests {
            .await;

        assert!(context2.is_configured().await?);
-        assert_eq!(
-            context2.get_config(Config::ConfiguredAddr).await?,
-            Some("alice@example.org".to_string())
-        );
        Ok(())
    }

@@ -1074,7 +1070,6 @@ mod tests {
            .await;

        assert!(!context2.is_configured().await?);
-        assert_eq!(context2.get_config(Config::ConfiguredAddr).await?, None);

        Ok(())
    }
@@ -124,15 +124,15 @@ pub trait DcKey: Serialize + Deserializable + Clone {
 }

 /// Converts secret key to public key.
+///
+/// `addr` is the address used in the User ID which is generated for compatibility.
+/// `relay_addrs` is the comma-separated list of relay addresses.
 pub(crate) fn secret_key_to_public_key(
-    context: &Context,
    mut signed_secret_key: SignedSecretKey,
    timestamp: u32,
    addr: &str,
    relay_addrs: &str,
 ) -> Result<SignedPublicKey> {
-    info!(context, "Converting secret key to public key.");
-
    // Make sure timestamp of created signatures
    // is not in the past compared to the primary key timestamp.
    let timestamp = std::cmp::max(
@@ -305,7 +305,7 @@ pub(crate) async fn load_self_public_key_opt(context: &Context) -> Result<Option
    let addr = context.get_primary_self_addr().await?;
    let all_addrs = context.get_self_addrs().await?.join(",");
    let signed_public_key =
-        secret_key_to_public_key(context, signed_secret_key, timestamp, &addr, &all_addrs)?;
+        secret_key_to_public_key(signed_secret_key, timestamp, &addr, &all_addrs)?;
    *lock = Some(signed_public_key.clone());

    Ok(Some(signed_public_key))
@@ -660,7 +660,6 @@ mod tests {
    use std::time::Duration;

    use super::*;
-    use crate::config::Config;
    use crate::test_utils::{TestContext, TestContextManager, alice_keypair};
    use crate::tools::SystemTime;
    use crate::transport::add_pseudo_transport;
@@ -814,9 +813,6 @@ i8pcjGO+IZffvyZJVRWfVooBJmWWbPB1pueo3tx8w3+fcuzpxz+RLFKaPyqXO+dD
    async fn test_load_self_generate_public() {
        let t = TestContext::new().await;
        add_pseudo_transport(&t, "alice@example.org").await.unwrap();
-        t.set_config(Config::ConfiguredAddr, Some("alice@example.org"))
-            .await
-            .unwrap();
        let key = load_self_public_key(&t).await;
        assert!(key.is_ok());
    }
@@ -825,9 +821,6 @@ i8pcjGO+IZffvyZJVRWfVooBJmWWbPB1pueo3tx8w3+fcuzpxz+RLFKaPyqXO+dD
    async fn test_load_self_generate_secret() {
        let t = TestContext::new().await;
        add_pseudo_transport(&t, "alice@example.org").await.unwrap();
-        t.set_config(Config::ConfiguredAddr, Some("alice@example.org"))
-            .await
-            .unwrap();
        let key = load_self_secret_key(&t).await;
        assert!(key.is_ok());
    }
@@ -838,9 +831,6 @@ i8pcjGO+IZffvyZJVRWfVooBJmWWbPB1pueo3tx8w3+fcuzpxz+RLFKaPyqXO+dD

        let t = TestContext::new().await;
        add_pseudo_transport(&t, "alice@example.org").await.unwrap();
-        t.set_config(Config::ConfiguredAddr, Some("alice@example.org"))
-            .await
-            .unwrap();
        let thr0 = {
            let ctx = t.clone();
            thread::spawn(move || {
@@ -188,13 +188,25 @@ pub(crate) async fn maybe_send_keyupdate_message(context: &Context) -> Result<()
    }

    let recipients = keyupdate_recipients(context, KEYUPDATE_MAX_RECIPIENTS).await?;
-    for chunk in recipients.chunks(KEYUPDATE_CHUNK_CONTACTS) {
-        let envelope = envelope_recipients(chunk);
-        let rfc724_mid = create_outgoing_rfc724_mid();
-        let keys = chunk.iter().map(|r| r.public_key.clone()).collect();
-        let queued_msg = keyupdate_message(context, &rfc724_mid, keys, envelope).await?;
-        insert_into_smtp(context, &rfc724_mid, &queued_msg).await?;
-    }
+    info!(
+        context,
+        "Sending keyupdate messages to {} recipients.",
+        recipients.len()
+    );
+    let is_bot = context.get_config_bool(Config::Bot).await?;
+    context
+        .sql
+        .transaction(|tx| {
+            for chunk in recipients.chunks(KEYUPDATE_CHUNK_CONTACTS) {
+                let envelope = envelope_recipients(chunk);
+                let rfc724_mid = create_outgoing_rfc724_mid();
+                let keys = chunk.iter().map(|r| r.public_key.clone()).collect();
+                let queued_msg = keyupdate_message(is_bot, &rfc724_mid, keys, envelope);
+                insert_into_smtp(tx, &rfc724_mid, &queued_msg)?;
+            }
+            Ok(())
+        })
+        .await?;

    // Record only after queueing, so failed queueing is retried by a later check.
    context
@@ -260,10 +260,6 @@ async fn test_keyupdate_on_replacement() -> Result<()> {
    alice.add_transport("alice@relay.example.net").await;
    SystemTime::shift(Duration::from_secs(2));
    alice.delete_transport("alice@example.org").await?;
-    assert_eq!(
-        alice.get_config(Config::ConfiguredAddr).await?.as_deref(),
-        Some("alice@relay.example.net")
-    );

    maybe_send_keyupdate_message(alice).await?;
    let keyupdate = alice.pop_sent_msg().await;
@@ -10,6 +10,7 @@ use deltachat_derive::{FromSql, ToSql};
 use humansize::BINARY;
 use humansize::format_size;
 use num_traits::FromPrimitive;
+use rusqlite::{OptionalExtension, Transaction};
 use serde::{Deserialize, Serialize};
 use tokio::{fs, io};

@@ -22,9 +23,9 @@ use crate::contact::{self, Contact, ContactId};
 use crate::context::Context;
 use crate::debug_logging::set_debug_logging_xdc;
 use crate::download::DownloadState;
-use crate::ephemeral::{Timer as EphemeralTimer, start_ephemeral_timers_msgids};
+use crate::ephemeral::Timer as EphemeralTimer;
 use crate::events::EventType;
-use crate::imap::markseen_on_imap_table;
+use crate::imap::insert_imap_markseen;
 use crate::location;
 use crate::log::warn;
 use crate::mimeparser::{SystemMessage, parse_message_id};
@@ -1777,87 +1778,69 @@ pub async fn markseen_msgs(context: &Context, msg_ids: Vec<MsgId>) -> Result<()>
        .set_config_internal(Config::LastMsgId, Some(&last_msg_id.to_u32().to_string()))
        .await?;

-    let mut msgs = Vec::with_capacity(msg_ids.len());
-    for &id in &msg_ids {
-        if let Some(msg) = context
-            .sql
-            .query_row_optional(
-                "SELECT
-                    m.chat_id AS chat_id,
-                    m.state AS state,
-                    m.ephemeral_timer AS ephemeral_timer,
-                    m.param AS param,
-                    m.from_id AS from_id,
-                    m.rfc724_mid AS rfc724_mid,
-                    m.hidden AS hidden,
-                    c.archived AS archived,
-                    c.blocked AS blocked
-                 FROM msgs m LEFT JOIN chats c ON c.id=m.chat_id
-                 WHERE m.id=? AND m.chat_id>9",
-                (id,),
-                |row| {
-                    let chat_id: ChatId = row.get("chat_id")?;
-                    let state: MessageState = row.get("state")?;
-                    let param: Params = row.get::<_, String>("param")?.parse().unwrap_or_default();
-                    let from_id: ContactId = row.get("from_id")?;
-                    let rfc724_mid: String = row.get("rfc724_mid")?;
-                    let hidden: bool = row.get("hidden")?;
-                    let visibility: ChatVisibility = row.get("archived")?;
-                    let blocked: Option<Blocked> = row.get("blocked")?;
-                    let ephemeral_timer: EphemeralTimer = row.get("ephemeral_timer")?;
-                    Ok((
-                        (
-                            id,
-                            chat_id,
-                            state,
-                            param,
-                            from_id,
-                            rfc724_mid,
-                            hidden,
-                            visibility,
-                            blocked.unwrap_or_default(),
-                        ),
-                        ephemeral_timer,
-                    ))
-                },
-            )
-            .await?
-        {
-            msgs.push(msg);
-        }
-    }
-
-    if msgs
-        .iter()
-        .any(|(_, ephemeral_timer)| *ephemeral_timer != EphemeralTimer::Disabled)
-    {
-        start_ephemeral_timers_msgids(context, &msg_ids)
-            .await
-            .context("failed to start ephemeral timers")?;
-    }
-
+    let should_send_mdns = context.should_send_mdns().await?;
+    let bcc_self = context.get_config_bool(Config::BccSelf).await?;
    let mut updated_chat_ids = BTreeSet::new();
    let mut archived_chats_maybe_noticed = false;
-    for (
-        (
-            id,
-            curr_chat_id,
-            curr_state,
-            curr_param,
-            curr_from_id,
-            curr_rfc724_mid,
-            curr_hidden,
-            curr_visibility,
-            curr_blocked,
-        ),
-        _curr_ephemeral_timer,
-    ) in msgs
-    {
-        if curr_state == MessageState::InFresh || curr_state == MessageState::InNoticed {
-            update_msg_state(context, id, MessageState::InSeen).await?;
+    let mut trigger_imap_interrupt = false;
+    let mut trigger_smtp_interrupt = false;
+    let mut trigger_ephemeral_interrupt = false;
+    let sql = &context.sql;
+    sql.transaction(|tx| {
+        for id in msg_ids {
+            let Some((
+                curr_chat_id,
+                curr_state,
+                curr_param,
+                curr_from_id,
+                curr_rfc724_mid,
+                curr_hidden,
+                curr_visibility,
+                curr_blocked,
+            )) = tx
+                .query_row(
+                    "SELECT
+                        m.chat_id AS chat_id,
+                        m.state AS state,
+                        m.param AS param,
+                        m.from_id AS from_id,
+                        m.rfc724_mid AS rfc724_mid,
+                        m.hidden AS hidden,
+                        c.archived AS archived,
+                        c.blocked AS blocked
+                     FROM msgs m LEFT JOIN chats c ON c.id=m.chat_id
+                     WHERE m.id=? AND m.chat_id>9",
+                    (id,),
+                    |row| {
+                        let chat_id: ChatId = row.get("chat_id")?;
+                        let state: MessageState = row.get("state")?;
+                        let param: Params =
+                            row.get::<_, String>("param")?.parse().unwrap_or_default();
+                        let from_id: ContactId = row.get("from_id")?;
+                        let rfc724_mid: String = row.get("rfc724_mid")?;
+                        let hidden: bool = row.get("hidden")?;
+                        let visibility: ChatVisibility = row.get("archived")?;
+                        let blocked: Option<Blocked> = row.get("blocked")?;
+                        let blocked = blocked.unwrap_or_default();
+                        Ok((
+                            chat_id, state, param, from_id, rfc724_mid, hidden, visibility,
+                            blocked,
+                        ))
+                    },
+                )
+                .optional()?
+            else {
+                continue;
+            };
+            trigger_ephemeral_interrupt |= id.start_ephemeral_timer(tx)?;
+            if !matches!(curr_state, MessageState::InFresh | MessageState::InNoticed) {
+                continue;
+            }
+            update_msg_state(tx, id, MessageState::InSeen)?;
            info!(context, "Seen message {}.", id);

-            markseen_on_imap_table(context, &curr_rfc724_mid).await?;
+            insert_imap_markseen(tx, &curr_rfc724_mid)?;
+            trigger_imap_interrupt = true;

            // Read receipts for system messages are never sent to contacts.
            // These messages have no place to display received read receipt
@@ -1874,21 +1857,18 @@ pub async fn markseen_msgs(context: &Context, msg_ids: Vec<MsgId>) -> Result<()>
                && !curr_hidden
                && wants_mdn
                && curr_param.get_cmd() == SystemMessage::Unknown
-                && context.should_send_mdns().await?
+                && should_send_mdns
            {
                // Clear WantsMdn to not handle a MDN twice
                // if the state later is InFresh again as markfresh_chat() was called.
                // BccSelf MDN messages in the next branch may be sent twice for syncing.
-                context
-                    .sql
-                    .execute(
-                        "UPDATE msgs SET param=? WHERE id=?",
-                        (curr_param.clone().remove(Param::WantsMdn).to_string(), id),
-                    )
-                    .await
-                    .context("failed to clear WantsMdn")?;
+                tx.execute(
+                    "UPDATE msgs SET param=? WHERE id=?",
+                    (curr_param.clone().remove(Param::WantsMdn).to_string(), id),
+                )
+                .context("failed to clear WantsMdn")?;
                Some(curr_from_id)
-            } else if context.get_config_bool(Config::BccSelf).await? {
+            } else if bcc_self {
                Some(ContactId::SELF)
            } else {
                None
@@ -1899,24 +1879,32 @@ pub async fn markseen_msgs(context: &Context, msg_ids: Vec<MsgId>) -> Result<()>
                    "Queuing MDN to {to_id} for {id} from {curr_from_id}, wants_mdn={wants_mdn}, cmd={}.",
                    curr_param.get_cmd()
                );
-                context
-                    .sql
-                    .execute(
-                        "INSERT INTO smtp_mdns (msg_id, from_id, rfc724_mid) VALUES(?, ?, ?)",
-                        (id, to_id, curr_rfc724_mid),
-                    )
-                    .await
-                    .context("failed to insert into smtp_mdns")?;
-                context.scheduler.interrupt_smtp().await;
+                tx.execute(
+                    "INSERT INTO smtp_mdns (msg_id, from_id, rfc724_mid) VALUES(?, ?, ?)",
+                    (id, to_id, curr_rfc724_mid),
+                )
+                .context("failed to insert into smtp_mdns")?;
+                trigger_smtp_interrupt = true;
            }

            if !curr_hidden {
                updated_chat_ids.insert(curr_chat_id);
            }
+            archived_chats_maybe_noticed |= curr_state == MessageState::InFresh
+                && !curr_hidden
+                && curr_visibility == ChatVisibility::Archived;
        }
-        archived_chats_maybe_noticed |= curr_state == MessageState::InFresh
-            && !curr_hidden
-            && curr_visibility == ChatVisibility::Archived;
+        Ok(())
+    })
+    .await?;
+    if trigger_imap_interrupt {
+        context.scheduler.interrupt_inbox().await;
+    }
+    if trigger_smtp_interrupt {
+        context.scheduler.interrupt_smtp().await;
+    }
+    if trigger_ephemeral_interrupt {
+        context.scheduler.interrupt_ephemeral_task().await;
    }

    for updated_chat_id in updated_chat_ids {
@@ -1957,11 +1945,7 @@ pub async fn get_existing_msg_ids(context: &Context, ids: &[MsgId]) -> Result<Ve
    Ok(res)
 }

-pub(crate) async fn update_msg_state(
-    context: &Context,
-    msg_id: MsgId,
-    state: MessageState,
-) -> Result<()> {
+pub(crate) fn update_msg_state(tx: &Transaction, msg_id: MsgId, state: MessageState) -> Result<()> {
    ensure!(
        state != MessageState::OutMdnRcvd,
        "Update msgs_mdns table instead!"
@@ -1971,13 +1955,10 @@ pub(crate) async fn update_msg_state(
        true => ", error=''",
        false => "",
    };
-    context
-        .sql
-        .execute(
-            &format!("UPDATE msgs SET state=? {error_subst} WHERE id=?"),
-            (state, msg_id),
-        )
-        .await?;
+    tx.execute(
+        &format!("UPDATE msgs SET state=? {error_subst} WHERE id=?"),
+        (state, msg_id),
+    )?;
    Ok(())
 }

@@ -2020,18 +2001,16 @@ pub(crate) async fn set_msg_failed(
 /// With `on_server`, copies seen on IMAP later are deleted on the server.
 ///
 /// Returns tombstone database row ID.
-pub(crate) async fn insert_tombstone(
-    context: &Context,
+pub(crate) fn insert_tombstone(
+    tx: &mut rusqlite::Transaction<'_>,
    rfc724_mid: &str,
    on_server: bool,
 ) -> Result<MsgId> {
-    let row_id = context
-        .sql
-        .insert(
-            "INSERT INTO msgs(rfc724_mid, chat_id, deleted) VALUES (?,?,?)",
-            (rfc724_mid, ChatId::TRASH, on_server),
-        )
-        .await?;
+    tx.execute(
+        "INSERT INTO msgs(rfc724_mid, chat_id, deleted) VALUES (?,?,?)",
+        (rfc724_mid, ChatId::TRASH, on_server),
+    )?;
+    let row_id = tx.last_insert_rowid();
    let msg_id = MsgId::new(u32::try_from(row_id)?);
    Ok(msg_id)
 }
@@ -316,6 +316,24 @@ async fn test_markseen_msgs() -> Result<()> {
    Ok(())
 }

+/// Tests that a read receipt failing to be queued is queued by the next `markseen_msgs()`.
+#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+async fn test_markseen_msgs_failed_mdn_retried() -> Result<()> {
+    let mut tcm = TestContextManager::new();
+    let alice = &tcm.alice().await;
+    let bob = &tcm.bob().await;
+    let msg = tcm.send_recv_accept(alice, bob, "hi").await;
+
+    let sql = &bob.sql;
+    sql.execute("ALTER TABLE smtp_mdns RENAME TO t", ()).await?;
+    assert!(markseen_msgs(bob, vec![msg.id]).await.is_err());
+    sql.execute("ALTER TABLE t RENAME TO smtp_mdns", ()).await?;
+
+    markseen_msgs(bob, vec![msg.id]).await?;
+    assert!(sql.exists("SELECT COUNT(*) FROM smtp_mdns", ()).await?);
+    Ok(())
+}
+
 /// Message has been seen on another device when fully downloaded. `state` should be updated.
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn test_msg_seen_on_imap_when_downloaded() -> Result<()> {
@@ -347,16 +347,15 @@ pub(crate) fn render_queued_mail(
                // <https://www.rfc-editor.org/rfc/rfc9787.html#structural-header-fields>.
                continue;
            }
-            let header_value =
-                if header_name == "chat-version" || header_name == "chat-is-post-message" {
-                    parsed_header.get_value_raw()
-                } else if header_name == "subject" {
-                    &b"[...]"[..]
-                } else if header_name == "to" {
-                    &b"\"hidden-recipients\": ;"[..]
-                } else {
-                    continue;
-                };
+            let header_value = if header_name == "chat-is-post-message" {
+                parsed_header.get_value_raw()
+            } else if header_name == "subject" {
+                &b"[...]"[..]
+            } else if header_name == "to" {
+                &b"\"hidden-recipients\": ;"[..]
+            } else {
+                continue;
+            };

            outer_headers.extend(original_header_name.as_bytes());
            outer_headers.extend(b": ");
@@ -433,9 +432,9 @@ pub(crate) fn render_queued_mail(
 #[cfg(test)]
 pub(crate) async fn render_queued_mail_with_context(
    queued_mail: QueuedMail,
-    context: &Context,
+    context: &crate::test_utils::TestContext,
 ) -> Result<RenderedEmail> {
-    let from_addr = context.get_primary_self_addr().await?;
+    let from_addr = context.sending_addr().await;
    let public_key = crate::key::load_self_public_key(context).await?;
    let secret_key = crate::key::load_self_secret_key(context).await?;

@@ -999,14 +998,10 @@ impl MimeFactory {
            true => context.get_config(Config::Displayname).await?,
            false => None,
        };
-        let self_name = &match self_name {
-            Some(name) => name,
-            None => context
-                .get_config(Config::ConfiguredAddr)
-                .await?
-                .unwrap_or_default(),
-        };
-        Ok(stock_str::subject_for_new_contact(context, self_name))
+        Ok(stock_str::subject_for_new_contact(
+            context,
+            self_name.as_deref().unwrap_or("..."),
+        ))
    }

    pub fn recipients(&self) -> Vec<String> {
@@ -1228,7 +1223,7 @@ impl MimeFactory {
    ///
    /// Used only for tests.
    #[cfg(test)]
-    pub async fn render(self, context: &Context) -> Result<RenderedEmail> {
+    pub async fn render(self, context: &crate::test_utils::TestContext) -> Result<RenderedEmail> {
        // Does not matter, we are not going to return the QueuedMail.
        let bcc_self = false;
        let (queued_mail, _side_effects) =
@@ -2174,10 +2169,7 @@ fn b_encode(value: &str) -> String {

 /// Returns the headers to place into the encrypted part
 /// of messages that are not part of a chat.
-async fn non_chat_headers(
-    context: &Context,
-    subject: &str,
-) -> Result<Vec<(&'static str, HeaderType<'static>)>> {
+fn non_chat_headers(is_bot: bool, subject: &str) -> Vec<(&'static str, HeaderType<'static>)> {
    let date = chrono::DateTime::<chrono::Utc>::from_timestamp(time(), 0)
        .unwrap()
        .to_rfc2822();
@@ -2187,10 +2179,10 @@ async fn non_chat_headers(
        ("Subject", Text::new(subject.to_string()).into()),
    ];
    // Automatic Response headers <https://www.rfc-editor.org/rfc/rfc3834>
-    if context.get_config_bool(Config::Bot).await? {
+    if is_bot {
        headers.push(("Auto-Submitted", Raw::new("auto-generated").into()));
    }
-    Ok(headers)
+    headers
 }

 pub(crate) async fn symm_encrypted_securejoin_message(
@@ -2206,7 +2198,8 @@ pub(crate) async fn symm_encrypted_securejoin_message(

    let message: MimePart<'static> = MimePart::new("text/plain", "Secure-Join");

-    let mut headers = non_chat_headers(context, "Secure-Join").await?;
+    let is_bot = context.get_config_bool(Config::Bot).await?;
+    let mut headers = non_chat_headers(is_bot, "Secure-Join");
    headers.push(("Secure-Join", Raw::new(step.to_string()).into()));
    headers.push(("Secure-Join-Auth", Text::new(auth.to_string()).into()));

@@ -2384,23 +2377,18 @@ fn keyupdate_body() -> MimePart<'static> {

 /// Returns a keyupdate message informing the owners of `recipient_keys`
 /// about the current key and relay list, see [`crate::keyupdate`].
-pub(crate) async fn keyupdate_message(
-    context: &Context,
+pub(crate) fn keyupdate_message(
+    is_bot: bool,
    rfc724_mid: &str,
    recipient_keys: Vec<SignedPublicKey>,
    recipients: Vec<String>,
-) -> Result<QueuedMail> {
-    info!(
-        context,
-        "Sending keyupdate message to {} recipients.",
-        recipient_keys.len()
-    );
+) -> QueuedMail {
    let message = keyupdate_body();

-    let headers = non_chat_headers(context, "Keyupdate").await?;
+    let headers = non_chat_headers(is_bot, "Keyupdate");
    let message = add_headers_to_encrypted_part(message, headers);

-    let queued_mail = QueuedMail {
+    QueuedMail {
        raw_message: part_to_bytes(message),
        display_name: String::new(),
        rfc724_mid: rfc724_mid.to_string(),
@@ -2420,8 +2408,7 @@ pub(crate) async fn keyupdate_message(
        recipients,
        sent_to: Vec::new(),
        bcc_self: false,
-    };
-    Ok(queued_mail)
+    }
 }

 /// Renders MIME part into a vector of bytes.
@@ -185,7 +185,7 @@ async fn test_subject_outgoing() {
    let t = TestContext::new_alice().await;
    t.allow_unencrypted().await.unwrap();

-    assert_eq!(first_subject_str(t).await, "Message from alice@example.org");
+    assert_eq!(first_subject_str(t).await, "Message from ...");

    let t = TestContext::new_alice().await;
    t.allow_unencrypted().await.unwrap();
@@ -362,7 +362,6 @@ async fn test_mdn_sent_to_all_relays() -> Result<()> {
    // Bob's key gets a second relay address and Alice merges the newer key.
    let bob_secret_key = load_self_secret_key(bob).await?;
    let bob_public_key = secret_key_to_public_key(
-        bob,
        bob_secret_key,
        u32::try_from(time())? + 100,
        "bob@example.net",
@@ -732,9 +731,9 @@ async fn test_remove_member_bcc() -> Result<()> {
    let charlie = &tcm.charlie().await;
    alice.allow_unencrypted().await?;

-    let alice_addr = alice.get_config(Config::ConfiguredAddr).await?.unwrap();
-    let bob_addr = bob.get_config(Config::ConfiguredAddr).await?.unwrap();
-    let charlie_addr = charlie.get_config(Config::ConfiguredAddr).await?.unwrap();
+    let alice_addr = alice.get_primary_self_addr().await?;
+    let bob_addr = bob.get_primary_self_addr().await?;
+    let charlie_addr = charlie.get_primary_self_addr().await?;

    let bob_id = alice.add_or_lookup_address_contact_id(bob).await;
    let charlie_id = alice.add_or_lookup_address_contact_id(charlie).await;
@@ -897,7 +896,7 @@ async fn test_new_member_is_first_recipient() -> Result<()> {
    assert!(
        sent_msg
            .recipients
-            .starts_with(&charlie.get_config(Config::ConfiguredAddr).await?.unwrap())
+            .starts_with(&charlie.get_primary_self_addr().await?)
    );

    remove_contact_from_chat(alice, group, bob_id).await?;
@@ -905,11 +904,8 @@ async fn test_new_member_is_first_recipient() -> Result<()> {
    SystemTime::shift(Duration::from_secs(60));
    add_contact_to_chat(alice, group, bob_id).await?;
    let sent_msg = alice.pop_sent_msg().await;
-    assert!(
-        sent_msg
-            .recipients
-            .starts_with(&bob.get_config(Config::ConfiguredAddr).await?.unwrap())
-    );
+    let bob_addr = bob.get_primary_self_addr().await?;
+    assert!(sent_msg.recipients.starts_with(&bob_addr));
    Ok(())
 }

@@ -1059,7 +1055,6 @@ Message-ID: <MESSAGE_ID@localhost>
 MIME-Version: 1.0
 To: "hidden-recipients": ;
 Subject: [...]
-Chat-Version: 1.0
 Content-Type: multipart/encrypted; protocol="application/pgp-encrypted";
 boundary="BOUNDARY"

@@ -1117,7 +1112,7 @@ Autocrypt: addr=alice@example.org; prefer-encrypt=mutual;
 Content-Type: text/plain; charset="utf-8"
 Date: DATE
 To: <bob@example.net>
-Subject: Message from alice@example.org
+Subject: Message from ...
 References: <MESSAGE_ID@localhost>
 Chat-Version: 1.0
 Content-Transfer-Encoding: 7bit
@@ -1169,7 +1164,7 @@ Content-Type: multipart/mixed;
 boundary="BOUNDARY"
 Date: DATE
 To: <bob@example.net>
-Subject: Message from alice@example.org
+Subject: Message from ...
 References: <MESSAGE_ID@localhost>
 Chat-Version: 1.0

@@ -701,7 +701,6 @@ impl MimeMessage {
        Ok(parser)
    }

-    #[expect(clippy::arithmetic_side_effects)]
    fn get_timestamp_sent(
        hdrs: &[mailparse::MailHeader<'_>],
        default: i64,
@@ -710,7 +709,10 @@ impl MimeMessage {
        hdrs.get_header_value(HeaderDef::Date)
            .and_then(|v| mailparse::dateparse(&v).ok())
            .map_or(default, |value| {
-                min(value, timestamp_rcvd + constants::TIMESTAMP_SENT_TOLERANCE)
+                min(
+                    value,
+                    timestamp_rcvd.saturating_add(constants::TIMESTAMP_SENT_TOLERANCE),
+                )
            })
    }

@@ -970,7 +972,6 @@ impl MimeMessage {
        Ok(())
    }

-    #[expect(clippy::arithmetic_side_effects)]
    fn avatar_action_from_header(
        &mut self,
        context: &Context,
@@ -990,23 +991,19 @@ impl MimeMessage {
                    None
                }
            }
+        } else if let Some(i) = self
+            .parts
+            .iter()
+            .position(|part| part.org_filename.as_ref() == Some(&header_value))
+        {
+            // Previous versions of Delta Chat sent avatars as attachments
+            // with the filename of the attachment sent in the Chat-User-Avatar header.
+            self.parts
+                .remove(i)
+                .param
+                .get(Param::File)
+                .map(|blob| AvatarAction::Change(blob.to_string()))
        } else {
-            // Avatar sent in attachment, as previous versions of Delta Chat did.
-
-            let mut i = 0;
-            while let Some(part) = self.parts.get_mut(i) {
-                if let Some(part_filename) = &part.org_filename
-                    && part_filename == &header_value
-                {
-                    if let Some(blob) = part.param.get(Param::File) {
-                        let res = Some(AvatarAction::Change(blob.to_string()));
-                        self.parts.remove(i);
-                        return Ok(res);
-                    }
-                    break;
-                }
-                i += 1;
-            }
            None
        };
        Ok(res)
@@ -1367,7 +1364,7 @@ impl MimeMessage {
                        self.do_add_single_part(part);
                        return Ok(true);
                    }
-                    mime::TEXT | mime::HTML => {
+                    mime::TEXT => {
                        let decoded_data = match mail.get_body() {
                            Ok(decoded_data) => decoded_data,
                            Err(err) => {
@@ -1490,7 +1487,6 @@ impl MimeMessage {
    }

    #[expect(clippy::too_many_arguments)]
-    #[expect(clippy::arithmetic_side_effects)]
    async fn do_add_single_file_part(
        &mut self,
        context: &Context,
@@ -1565,7 +1561,11 @@ impl MimeMessage {
        {
            match get_filemeta(decoded_data) {
                // image size is known, not too big, keep msg_type:
-                Ok((width, height)) if width * height <= constants::MAX_RCVD_IMAGE_PIXELS => {
+                Ok((width, height))
+                    if width
+                        .checked_mul(height)
+                        .is_some_and(|pixels| pixels <= constants::MAX_RCVD_IMAGE_PIXELS) =>
+                {
                    part.param.set_i64(Param::Width, width.into());
                    part.param.set_i64(Param::Height, height.into());
                    msg_type
@@ -2045,9 +2045,8 @@ impl MimeMessage {
    /// Returns parsed `Chat-Group-Member-Timestamps` header contents.
    ///
    /// Returns `None` if there is no such header.
-    #[expect(clippy::arithmetic_side_effects)]
    pub fn chat_group_member_timestamps(&self) -> Option<Vec<i64>> {
-        let now = time() + constants::TIMESTAMP_SENT_TOLERANCE;
+        let now = time().saturating_add(constants::TIMESTAMP_SENT_TOLERANCE);
        self.get_header(HeaderDef::ChatGroupMemberTimestamps)
            .map(|h| {
                h.split_ascii_whitespace()
@@ -2228,3 +2228,27 @@ async fn test_load_shared_secrets_with_legacy_state() -> Result<()> {

    Ok(())
 }
+
+/// Tests that MIME parts with html/* MIME type are ignored.
+///
+/// HTML parts should have a text/html MIME type.
+#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+async fn test_ignore_html_mime_parts() -> Result<()> {
+    let mut tcm = TestContextManager::new();
+    let alice = &tcm.alice().await;
+    let bob = &tcm.bob().await;
+    let encrypted_msg = test_utils::encrypt_raw_message(
+        bob,
+        &[alice],
+        include_bytes!("../../test-data/message/html_html_mime.eml"),
+    )
+    .await?;
+
+    let msg = MimeMessage::from_bytes(alice, encrypted_msg.as_bytes()).await?;
+    assert_eq!(msg.parts.len(), 1);
+    assert_eq!(msg.parts[0].typ, Viewtype::Text);
+    assert_eq!(msg.parts[0].mimetype, Some(mime::TEXT_PLAIN));
+    assert_eq!(msg.parts[0].msg, "Here is a text part.");
+
+    Ok(())
+}
@@ -131,7 +131,7 @@ async fn test_broadcast_security_attacker_signature() -> Result<()> {

    let secret = load_broadcast_secret(alice, alice_chat_id).await?.unwrap();

-    let charlie_addr = charlie.get_config(Config::ConfiguredAddr).await?.unwrap();
+    let charlie_addr = charlie.get_primary_self_addr().await?;

    test_shared_secret_decryption_ext(
        bob,
@@ -183,7 +183,7 @@ async fn test_broadcast_security_happy_path() -> Result<()> {

    let secret = load_broadcast_secret(alice, alice_chat_id).await?.unwrap();

-    let alice_addr = alice.get_config(Config::ConfiguredAddr).await?.unwrap();
+    let alice_addr = alice.get_primary_self_addr().await?;

    test_shared_secret_decryption_ext(bob, &alice_addr, &secret, Some(alice), None).await
 }
@@ -202,7 +202,7 @@ async fn test_qr_code_security() -> Result<()> {
    // Start a securejoin process, but don't finish it:
    join_securejoin(bob, &qr).await?;

-    let charlie_addr = charlie.get_config(Config::ConfiguredAddr).await?.unwrap();
+    let charlie_addr = charlie.get_primary_self_addr().await?;

    let alice_fp = self_fingerprint(alice).await?;
    let secret_for_encryption = format!("securejoin/{alice_fp}/{authcode}");
@@ -316,10 +316,6 @@ static DNS_PRELOAD: LazyLock<HashMap<&'static str, Vec<IpAddr>>> = LazyLock::new
            "mail.buzon.uy",
            vec![IpAddr::V4(Ipv4Addr::new(200, 40, 115, 74))],
        ),
-        (
-            "daleth.cafe",
-            vec![IpAddr::V4(Ipv4Addr::new(37, 27, 6, 204))],
-        ),
        (
            "disroot.org",
            vec![IpAddr::V4(Ipv4Addr::new(178, 21, 23, 139))],
@@ -680,6 +676,7 @@ static DNS_PRELOAD: LazyLock<HashMap<&'static str, Vec<IpAddr>>> = LazyLock::new
            ],
        ),
        // Known public chatmail relays from https://chatmail.at/relays
+        // and default onboarding relays.
        (
            "mehl.cloud",
            vec![IpAddr::V4(Ipv4Addr::new(95, 217, 223, 172))],
@@ -688,6 +685,10 @@ static DNS_PRELOAD: LazyLock<HashMap<&'static str, Vec<IpAddr>>> = LazyLock::new
            "mailchat.pl",
            vec![IpAddr::V4(Ipv4Addr::new(46, 62, 144, 137))],
        ),
+        (
+            "nchrcht.la10cy.net",
+            vec![IpAddr::V4(Ipv4Addr::new(217, 197, 86, 157))],
+        ),
        (
            "chatmail.woodpeckersnest.space",
            vec![IpAddr::V4(Ipv4Addr::new(85, 215, 162, 146))],
@@ -704,6 +705,10 @@ static DNS_PRELOAD: LazyLock<HashMap<&'static str, Vec<IpAddr>>> = LazyLock::new
            "chat.adminforge.de",
            vec![IpAddr::V4(Ipv4Addr::new(94, 130, 17, 142))],
        ),
+        (
+            "chat.me.ke",
+            vec![IpAddr::V4(Ipv4Addr::new(169, 255, 58, 122))],
+        ),
        (
            "chika.aangat.lahat.computer",
            vec![IpAddr::V4(Ipv4Addr::new(71, 19, 150, 113))],
@@ -725,8 +730,20 @@ static DNS_PRELOAD: LazyLock<HashMap<&'static str, Vec<IpAddr>>> = LazyLock::new
            vec![IpAddr::V4(Ipv4Addr::new(45, 124, 54, 79))],
        ),
        (
-            "sombras.chat",
-            vec![IpAddr::V4(Ipv4Addr::new(82, 25, 70, 154))],
+            "chatmail.cc",
+            vec![IpAddr::V4(Ipv4Addr::new(15, 235, 198, 20))],
+        ),
+        (
+            "deltachat.me",
+            vec![IpAddr::V4(Ipv4Addr::new(102, 68, 86, 134))],
+        ),
+        (
+            "e2e.sus.fr",
+            vec![IpAddr::V4(Ipv4Addr::new(93, 95, 231, 235))],
+        ),
+        (
+            "chatmail.uk",
+            vec![IpAddr::V4(Ipv4Addr::new(213, 165, 89, 146))],
        ),
        (
            "e2ee.wang",
@@ -736,7 +753,7 @@ static DNS_PRELOAD: LazyLock<HashMap<&'static str, Vec<IpAddr>>> = LazyLock::new
            "chat.privittytech.com",
            vec![IpAddr::V4(Ipv4Addr::new(35, 154, 144, 0))],
        ),
-        ("e2ee.im", vec![IpAddr::V4(Ipv4Addr::new(45, 137, 99, 57))]),
+        ("e2ee.im", vec![IpAddr::V4(Ipv4Addr::new(45, 137, 99, 156))]),
        (
            "chatmail.email",
            vec![IpAddr::V4(Ipv4Addr::new(57, 128, 220, 120))],
@@ -753,6 +770,10 @@ static DNS_PRELOAD: LazyLock<HashMap<&'static str, Vec<IpAddr>>> = LazyLock::new
            "chat.nuvon.app",
            vec![IpAddr::V4(Ipv4Addr::new(178, 238, 38, 165))],
        ),
+        (
+            "chat.tinydispatch.org",
+            vec![IpAddr::V4(Ipv4Addr::new(88, 198, 181, 62))],
+        ),
        (
            "nibblehole.com",
            vec![IpAddr::V4(Ipv4Addr::new(94, 247, 42, 209))],
@@ -761,10 +782,6 @@ static DNS_PRELOAD: LazyLock<HashMap<&'static str, Vec<IpAddr>>> = LazyLock::new
            "chat.zashm.org",
            vec![IpAddr::V4(Ipv4Addr::new(91, 245, 76, 39))],
        ),
-        (
-            "chat.sus.fr",
-            vec![IpAddr::V4(Ipv4Addr::new(152, 67, 76, 190))],
-        ),
        (
            "delta.thelab.uno",
            vec![IpAddr::V4(Ipv4Addr::new(146, 59, 228, 39))],
@@ -779,16 +796,12 @@ static DNS_PRELOAD: LazyLock<HashMap<&'static str, Vec<IpAddr>>> = LazyLock::new
        ),
        (
            "sweetfern.net",
-            vec![IpAddr::V4(Ipv4Addr::new(178, 156, 228, 133))],
+            vec![IpAddr::V4(Ipv4Addr::new(51, 81, 78, 167))],
        ),
        (
            "delta.disobey.net",
            vec![IpAddr::V4(Ipv4Addr::new(37, 74, 102, 44))],
        ),
-        (
-            "darkrun.dev",
-            vec![IpAddr::V4(Ipv4Addr::new(72, 11, 149, 146))],
-        ),
    ])
 });

@@ -23,7 +23,7 @@
 //!    (scoped per WebXDC app instance/message-id). The other peers can then join the gossip with `joinRealtimeChannel().setListener()`
 //!    and `joinRealtimeChannel().send()` just like the other peers.

-use anyhow::{Context as _, Result, anyhow, bail};
+use anyhow::{Context as _, Result, anyhow};
 use data_encoding::BASE32_NOPAD;
 use futures_lite::StreamExt;
 use iroh::{Endpoint, NodeAddr, NodeId, PublicKey, RelayMode, RelayUrl, SecretKey};
@@ -38,7 +38,6 @@ use url::Url;

 use crate::EventType;
 use crate::chat::send_msg;
-use crate::config::Config;
 use crate::context::Context;
 use crate::log::warn;
 use crate::message::{Message, MsgId, Viewtype};
@@ -299,10 +298,6 @@ impl Context {
    pub async fn get_or_try_init_peer_channel(
        &self,
    ) -> Result<tokio::sync::RwLockReadGuard<'_, Iroh>> {
-        if !self.get_config_bool(Config::WebxdcRealtimeEnabled).await? {
-            bail!("Attempt to initialize Iroh when realtime is disabled");
-        }
-
        if let Some(lock) = self.get_peer_channels().await {
            return Ok(lock);
        }
@@ -360,13 +355,6 @@ pub async fn add_gossip_peer_from_header(
    instance_id: MsgId,
    node_addr: &str,
 ) -> Result<()> {
-    if !context
-        .get_config_bool(Config::WebxdcRealtimeEnabled)
-        .await?
-    {
-        return Ok(());
-    }
-
    let node_addr =
        serde_json::from_str::<NodeAddr>(node_addr).context("Failed to parse node address")?;

@@ -464,10 +452,6 @@ pub async fn send_webxdc_realtime_advertisement(
    ctx: &Context,
    msg_id: MsgId,
 ) -> Result<Option<oneshot::Receiver<()>>> {
-    if !ctx.get_config_bool(Config::WebxdcRealtimeEnabled).await? {
-        return Ok(None);
-    }
-
    let iroh = ctx.get_or_try_init_peer_channel().await?;
    let conn = iroh.join_and_subscribe_gossip(ctx, msg_id).await?;

@@ -483,10 +467,6 @@ pub async fn send_webxdc_realtime_advertisement(

 /// Send realtime data to other peers using iroh.
 pub async fn send_webxdc_realtime_data(ctx: &Context, msg_id: MsgId, data: Vec<u8>) -> Result<()> {
-    if !ctx.get_config_bool(Config::WebxdcRealtimeEnabled).await? {
-        return Ok(());
-    }
-
    let iroh = ctx.get_or_try_init_peer_channel().await?;
    iroh.send_webxdc_realtime_data(ctx, msg_id, data).await?;
    Ok(())
@@ -242,12 +242,6 @@ async fn test_can_reconnect() {
    let alice = &mut tcm.alice().await;
    let bob = &mut tcm.bob().await;

-    assert!(
-        alice
-            .get_config_bool(Config::WebxdcRealtimeEnabled)
-            .await
-            .unwrap()
-    );
    // Alice sends webxdc to bob
    let alice_chat = alice.create_chat(bob).await;
    let mut instance = Message::new(Viewtype::File);
@@ -588,49 +582,11 @@ async fn connect_alice_bob(
    }
 }

-#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
-async fn test_peer_channels_disabled() {
-    let mut tcm = TestContextManager::new();
-    let alice = &mut tcm.alice().await;
-
-    alice
-        .set_config_bool(Config::WebxdcRealtimeEnabled, false)
-        .await
-        .unwrap();
-
-    // creates iroh endpoint as side effect
-    send_webxdc_realtime_advertisement(alice, MsgId::new(1))
-        .await
-        .unwrap();
-
-    assert!(alice.ctx.iroh.read().await.is_none());
-
-    // creates iroh endpoint as side effect
-    send_webxdc_realtime_data(alice, MsgId::new(1), vec![])
-        .await
-        .unwrap();
-
-    assert!(alice.ctx.iroh.read().await.is_none());
-
-    leave_webxdc_realtime(alice, MsgId::new(1)).await.unwrap();
-
-    assert!(alice.ctx.iroh.read().await.is_none());
-
-    // This internal function should return error
-    // if accidentally called with the setting disabled.
-    assert!(alice.ctx.get_or_try_init_peer_channel().await.is_err());
-}
-
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn test_leave_webxdc_realtime_uninitialized() {
    let mut tcm = TestContextManager::new();
    let alice = &mut tcm.alice().await;

-    alice
-        .set_config_bool(Config::WebxdcRealtimeEnabled, true)
-        .await
-        .unwrap();
-
    assert!(alice.ctx.iroh.read().await.is_none());
    leave_webxdc_realtime(alice, MsgId::new(1)).await.unwrap();
    assert!(alice.ctx.iroh.read().await.is_none());
@@ -1,5 +1,6 @@
 //! OpenPGP helper module using [rPGP facilities](https://github.com/rpgp/rpgp).

+use std::cmp::Ordering;
 use std::collections::{HashMap, HashSet};
 use std::io::Cursor;

@@ -83,13 +84,64 @@ pub(crate) fn create_keypair(addr: EmailAddress) -> Result<SignedSecretKey> {

 /// Selects a subkey of the public key to use for encryption.
 ///
-/// Returns `None` if the public key cannot be used for encryption.
+/// The key is selected according to
+/// <https://www.ietf.org/archive/id/draft-autocrypt-openpgp-v2-cert-03.html#section-4.3-4>.
+/// If multiple keys are available, the one that will expire sooner is selected.
 ///
-/// TODO: take key flags and expiration dates into account
-fn select_pk_for_encryption(key: &SignedPublicKey) -> Option<&SignedPublicSubKey> {
+/// Returns `None` if the public key cannot be used for encryption.
+fn select_pk_for_encryption(now: u32, key: &SignedPublicKey) -> Option<&SignedPublicSubKey> {
    key.public_subkeys
        .iter()
-        .find(|subkey| subkey.algorithm().can_encrypt())
+        .filter(|subkey| subkey.algorithm().can_encrypt())
+        .filter_map(|subkey| {
+            // We take arbitrary signature here and don't try to select the newest one.
+            // Filtering out outdated and invalid signatures should happen during certificate merging.
+            let signature = subkey.signatures.first()?;
+
+            let key_flags = signature.key_flags();
+            if !key_flags.encrypt_comms() {
+                return None;
+            }
+
+            if let Some(expiration_duration) = signature
+                .key_expiration_time()
+                .filter(|duration| duration.as_secs() != 0)
+                && now
+                    > subkey
+                        .created_at()
+                        .as_secs()
+                        .saturating_add(expiration_duration.as_secs())
+            {
+                // Key is expired.
+                return None;
+            }
+            Some((subkey, signature))
+        })
+        .min_by(|(subkey1, signature1), (subkey2, signature2)| {
+            match (
+                signature1
+                    .key_expiration_time()
+                    .filter(|duration| duration.as_secs() != 0),
+                signature2
+                    .key_expiration_time()
+                    .filter(|duration| duration.as_secs() != 0),
+            ) {
+                (None, None) => Ordering::Equal,
+                (None, Some(_)) => Ordering::Greater,
+                (Some(_), None) => Ordering::Less,
+                (Some(expiration1), Some(expiration2)) => (subkey1
+                    .created_at()
+                    .as_secs()
+                    .saturating_add(expiration1.as_secs()))
+                .cmp(
+                    &(subkey2
+                        .created_at()
+                        .as_secs()
+                        .saturating_add(expiration2.as_secs())),
+                ),
+            }
+        })
+        .map(|(subkey, _signature)| subkey)
 }

 /// Version of SEIPD packet to use.
@@ -110,12 +162,13 @@ pub enum SeipdVersion {
 /// encrypted to `public_keys_for_encryption`.
 #[expect(clippy::arithmetic_side_effects)]
 fn signature_subpackets(
+    now: pgp::types::Timestamp,
    private_key_for_signing: &SignedSecretKey,
    public_keys_for_encryption: &[SignedPublicKey],
 ) -> Result<SubpacketConfig> {
    let mut hashed = Vec::with_capacity(1 + public_keys_for_encryption.len() + 1);
    hashed.push(Subpacket::critical(SubpacketData::SignatureCreationTime(
-        pgp::types::Timestamp::now(),
+        now,
    ))?);
    for key in public_keys_for_encryption {
        let data = SubpacketData::IntendedRecipientFingerprint(key.fingerprint());
@@ -151,10 +204,11 @@ pub fn pk_encrypt(
 ) -> Result<String> {
    tokio::task::block_in_place(|| {
        let mut rng = thread_rng();
+        let now = pgp::types::Timestamp::now();

        let pkeys = public_keys_for_encryption
            .iter()
-            .filter_map(select_pk_for_encryption);
+            .filter_map(|key| select_pk_for_encryption(now.as_secs(), key));

        let msg = MessageBuilder::from_bytes("", plain);
        let encoded_msg = match seipd_version {
@@ -166,7 +220,8 @@ pub fn pk_encrypt(
                }

                if let Some(secret_key) = private_key_for_signing {
-                    let subpkts = signature_subpackets(secret_key, &public_keys_for_encryption)?;
+                    let subpkts =
+                        signature_subpackets(now, secret_key, &public_keys_for_encryption)?;
                    let hash_algorithm = secret_key.hash_alg();
                    msg.sign_with_subpackets(
                        &**secret_key,
@@ -194,7 +249,8 @@ pub fn pk_encrypt(
                }

                if let Some(secret_key) = private_key_for_signing {
-                    let subpkts = signature_subpackets(secret_key, &public_keys_for_encryption)?;
+                    let subpkts =
+                        signature_subpackets(now, secret_key, &public_keys_for_encryption)?;
                    let hash_algorithm = secret_key.hash_alg();
                    msg.sign_with_subpackets(
                        &**secret_key,
@@ -326,6 +382,8 @@ pub fn symm_encrypt_message(
 /// or even have some packets maliciously dropped
 /// (for example, all encryption subkeys dropped)
 /// or restored from some older version of the certificate.
+///
+/// In case of ties, i.e. same timestamps, data from the new certificate is preferred.
 pub fn merge_openpgp_certificates(
    old_certificate: SignedPublicKey,
    new_certificate: SignedPublicKey,
@@ -485,7 +543,8 @@ pub(crate) fn relay_addrs(public_key: &SignedPublicKey, addr: &str) -> Vec<Strin

 /// Returns true if the key can be encrypted to, i.e. has an encryption subkey.
 pub(crate) fn pubkey_can_encrypt(public_key: &SignedPublicKey) -> bool {
-    select_pk_for_encryption(public_key).is_some()
+    let now = pgp::types::Timestamp::now();
+    select_pk_for_encryption(now.as_secs(), public_key).is_some()
 }

 /// Returns true if public key advertises SEIPDv2 feature.
@@ -2,15 +2,16 @@ use std::sync::LazyLock;
 use tokio::sync::OnceCell;

 use super::*;
+use crate::key::secret_key_to_public_key;
 use crate::transport::add_pseudo_transport;
 use crate::{
-    config::Config,
    decrypt,
    key::{load_self_public_key, self_fingerprint, store_self_keypair},
    mimefactory::{part_to_bytes, wrap_encrypted_part},
    test_utils::{TestContext, TestContextManager, alice_keypair, bob_keypair},
    token,
 };
+use chrono::{TimeZone as _, Utc};
 use pgp::composed::{Esk, Message};
 use pgp::packet::PublicKeyEncryptedSessionKey;

@@ -23,9 +24,6 @@ async fn decrypt_bytes(
    add_pseudo_transport(t, "alice@example.org")
        .await
        .expect("Failed to add pseudo transport");
-    t.set_config(Config::ConfiguredAddr, Some("alice@example.org"))
-        .await
-        .expect("Failed to configure address");

    for secret in auth_tokens_for_decryption {
        token::save(t, token::Namespace::Auth, None, secret, 0).await?;
@@ -387,6 +385,31 @@ fn test_merge_openpgp_certificates() {
    assert!(merge_openpgp_certificates(bob, alice).is_err());
 }

+/// Tests that Direct Key Signature from the new certificate is preferred
+/// when the timestamp is the same.
+#[test]
+fn test_merge_openpgp_certificates_tiebreak() -> Result<()> {
+    let secret_key = alice_keypair();
+    let timestamp = pgp::types::Timestamp::now();
+
+    let addr = "alice@example.net";
+    let relays1 = "alice@example.net,alice@example.org";
+    let relays2 = "alice@example.net,alice@example.com";
+
+    let public_key1 =
+        secret_key_to_public_key(secret_key.clone(), timestamp.as_secs(), addr, relays1)?;
+    let public_key2 = secret_key_to_public_key(secret_key, timestamp.as_secs(), addr, relays2)?;
+
+    let merge12 = merge_openpgp_certificates(public_key1.clone(), public_key2.clone())?;
+    let merge21 = merge_openpgp_certificates(public_key2.clone(), public_key1.clone())?;
+
+    assert_eq!(merge12, public_key2);
+    assert_eq!(merge21, public_key1);
+    assert_ne!(merge12, merge21);
+
+    Ok(())
+}
+
 /// Test PQC support.
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn test_pqc() -> Result<()> {
@@ -423,3 +446,212 @@ async fn test_securejoin_pqc_joiner() {

    tcm.execute_securejoin(bob, pqc).await;
 }
+
+/// Tests that public subkey selection for encryption respects key flags and prefers expring subkeys.
+///
+/// Non-encryption subkeys such as RSA subkey for authentication are ignored.
+#[test]
+fn test_select_pk_for_encryption() {
+    // Public key generated with GnuPG 2.4.9 with the following subkeys:
+    // 1. Auth-only RSA subkey (92E762B9084CA740).
+    // 2. Expired Curve25519 encryption subkey with 1-day expiration (C8F382BD0F35C49E)
+    // 3. Ed25519 signing subkey (F177AC3118F923CC).
+    // 4. Curve25519 encryption subkey with fingerprint (36188C6FFC8E267B)
+    // 5. Curve25519 encryption subkey with 1 year expiration, valid in the beginning of 2008, with key ID 9223FCEE7546CDE7
+    // 6. Curve25519 encryption subkey with no expiration (FD2C0567967223D8).
+    // Primary key is an Ed25519 not expiring key.
+    // Key 4 is the one that should be selected.
+
+    // Subkey 4 fingerprint.
+    let expected_fallback_fingerprint = "cdeb3ba3999bf7880f0ee1f536188c6ffc8e267b";
+
+    // Subkey 5 fingerprint, should be preferred to fallback when not expired.
+    let expected_expiring_fingerprint = "5133fab157c4a46ca41f6dc39223fcee7546cde7";
+
+    let alice_tpk_asc = "
+-----BEGIN PGP PUBLIC KEY BLOCK-----
+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==
+=AXAi
+-----END PGP PUBLIC KEY BLOCK-----
+    ";
+
+    let alice_tpk = SignedPublicKey::from_asc(alice_tpk_asc).unwrap();
+    let now = pgp::types::Timestamp::now();
+    let encryption_subkey = select_pk_for_encryption(now.as_secs(), &alice_tpk).unwrap();
+    assert_eq!(
+        encryption_subkey.fingerprint().to_string().as_str(),
+        expected_fallback_fingerprint
+    );
+
+    // If we pass 1199149200 as the `now` argument, which was in the beginning of 2008,
+    // then the expiring subkey is not yet expired and should be used.
+    let encryption_subkey = select_pk_for_encryption(1199149200, &alice_tpk).unwrap();
+    assert_eq!(
+        encryption_subkey.fingerprint().to_string().as_str(),
+        expected_expiring_fingerprint
+    );
+}
+
+/// Tests that key selection fails if there is only an expired subkey.
+#[test]
+fn test_select_only_expired_subkey() {
+    let alice_tpk_asc = "
+    -----BEGIN PGP PUBLIC KEY BLOCK-----
+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+=zWPq
+-----END PGP PUBLIC KEY BLOCK-----
+";
+
+    let alice_tpk = SignedPublicKey::from_asc(alice_tpk_asc).unwrap();
+    let now = pgp::types::Timestamp::now();
+
+    assert_eq!(select_pk_for_encryption(now.as_secs(), &alice_tpk), None);
+}
+
+/// Tests that the key with the closest expiration date is selected.
+#[test]
+fn test_expiring_subkey_selection() {
+    // The key has the following keys:
+    // 1. Primary non-expiring Ed25519 key created on 2025-01-01
+    // 2. Non-expiring subkey CE5FC3FD479E41F08069DCE6F6CAD4ADB9AF47F1 created on 2025-01-01
+    // 3. Subkey 10493EF4DBA7EE4D55C826A7634684D9BFEEB890 created on 2026-06-01 and expiring on 2026-07-01
+    // 4. Subkey 477650C13FA4842BAF2831BC41C2D560BE27B38D created on 2026-06-01 and expiring on 2026-06-15
+    // 5. Subkey AB92F4AFD46DDD7D31FB05151BE08A8089F67CA2 created on 2026-06-08 and expiring on 2026-06-22
+    let alice_tpk_asc = "
+    -----BEGIN PGP PUBLIC KEY BLOCK-----
+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+=RzZZ
+-----END PGP PUBLIC KEY BLOCK-----
+";
+
+    let alice_tpk = SignedPublicKey::from_asc(alice_tpk_asc).unwrap();
+
+    // Two-week subkey that was generated earlier is selected
+    // because it expires earlier, on 2026-06-15.
+    {
+        let ts = u32::try_from(
+            Utc.with_ymd_and_hms(2026, 6, 9, 0, 0, 0)
+                .unwrap()
+                .timestamp(),
+        )
+        .unwrap();
+        let subkey = select_pk_for_encryption(ts, &alice_tpk).unwrap();
+        assert_eq!(
+            subkey.fingerprint().to_string().as_str(),
+            "477650c13fa4842baf2831bc41c2d560be27b38d",
+        );
+    }
+
+    // Now both 477650C13FA4842BAF2831BC41C2D560BE27B38D expires
+    // and we switch to another subkey that expires on 2026-06-22.
+    {
+        let ts = u32::try_from(
+            Utc.with_ymd_and_hms(2026, 6, 16, 0, 0, 0)
+                .unwrap()
+                .timestamp(),
+        )
+        .unwrap();
+        let subkey = select_pk_for_encryption(ts, &alice_tpk).unwrap();
+        assert_eq!(
+            subkey.fingerprint().to_string().as_str(),
+            "ab92f4afd46ddd7d31fb05151be08a8089f67ca2",
+        );
+    }
+
+    // Now both two-week subkeys have expired and we switch to expiring subkey that expires on 2026-07-01.
+    {
+        let ts = u32::try_from(
+            Utc.with_ymd_and_hms(2026, 6, 23, 0, 0, 0)
+                .unwrap()
+                .timestamp(),
+        )
+        .unwrap();
+        let subkey = select_pk_for_encryption(ts, &alice_tpk).unwrap();
+        assert_eq!(
+            subkey.fingerprint().to_string().as_str(),
+            "10493ef4dba7ee4d55c826a7634684d9bfeeb890",
+        );
+    }
+
+    // All expiring subkeys are expired, switching to non-expiring subkey.
+    {
+        let ts = u32::try_from(
+            Utc.with_ymd_and_hms(2026, 7, 2, 0, 0, 0)
+                .unwrap()
+                .timestamp(),
+        )
+        .unwrap();
+        let subkey = select_pk_for_encryption(ts, &alice_tpk).unwrap();
+        assert_eq!(
+            subkey.fingerprint().to_string().as_str(),
+            "ce5fc3fd479e41f08069dce6f6cad4adb9af47f1",
+        );
+    }
+}
@@ -5,8 +5,9 @@
 //!
 //! Pinned messages are synchronized for all chat members by sending an info-message
 //! that refers the pinned message in the `In-Reply-To:` header.
-//! The info-message is only shown for pinning (not for unpinning).
-//! Unpinning is an action that does not require so much attention; internally it is a hidden info-message.
+//! Info-message are shown for both, pinning and unpinning;
+//! the latter is important as otherwise the message "Alice pinned a message." may look like a bug
+//! if there is nothing actually pinned as Bob unpinned for whatever reason afterwards.

 use anyhow::{Result, ensure};

@@ -50,9 +51,8 @@ pub async fn set_pinned_state(
    info_msg.text = if new_pinned_state {
        stock_str::msg_pinned(context, ContactId::SELF).await
    } else {
-        "Message unpinned.".to_string() // no need to localize, "unpinned" messages are not visible
+        stock_str::msg_unpinned(context, ContactId::SELF).await
    };
-    info_msg.hidden = !new_pinned_state;
    info_msg.in_reply_to = Some(msg.rfc724_mid.clone());
    info_msg.param.set_cmd(if new_pinned_state {
        SystemMessage::MessagePinned
@@ -76,21 +76,20 @@ async fn test_pinned_messages() -> Result<()> {
        assert!(set_pinned_state(alice, info_msg.id, true).await.is_err());

        // Unpin the initially pinned message.
-        // Before, send another message "Bar". To test, no visible info message is added this time,
-        let sent3 = alice.send_text(alice_chat_id, "Bar").await;
-
        set_pinned_state(alice, msg1.id, false).await?;
-        let sent4 = alice.pop_sent_msg().await;
+        let sent3 = alice.pop_sent_msg().await;
        assert!(!sent1.load_from_db().await.is_pinned());
        expect_pinned_message_event(alice, msg1.chat_id).await;

        let pinned = get_pinned_messages(alice, alice_chat_id).await?;
        assert!(pinned.is_empty());

-        let msg3 = sent3.load_from_db().await;
-        assert!(!msg3.is_info());
-        assert!(!msg3.is_pinned());
-        assert_eq!(alice.get_last_msg_id_in(msg3.chat_id).await, msg3.id); // last message is still "Bar", not an info message
+        let unpin_msg = sent3.load_from_db().await;
+        assert!(unpin_msg.is_info());
+        assert!(!unpin_msg.hidden);
+        assert_eq!(unpin_msg.get_info_type(), SystemMessage::MessageUnpinned);
+        assert_eq!(unpin_msg.text, "You unpinned a message.");
+        assert_eq!(alice.get_last_msg_id_in(msg1.chat_id).await, unpin_msg.id);

        if alice_chat_id != self_chat_id {
            // Bob receives message "Foo"
@@ -115,19 +114,19 @@ async fn test_pinned_messages() -> Result<()> {
            assert_eq!(info_msg.get_info_type(), SystemMessage::MessagePinned);
            assert!(info_msg.get_info_contact_id(bob).await?.is_none());

-            // Bob receives message "Bar" and hidden message to unpin message "Foo"
-            bob.recv_msg(&sent3).await;
-            bob.recv_msg_trash(&sent4).await;
+            // Bob receives the info message to unpin message "Foo"
+            let unpin_msg = bob.recv_msg(&sent3).await;
            expect_pinned_message_event(bob, msg1.chat_id).await;
            assert!(!Message::load_from_db(bob, msg1.id).await?.is_pinned());

            let pinned = get_pinned_messages(bob, msg1.chat_id).await?;
            assert!(pinned.is_empty());

-            let no_info_msg =
-                Message::load_from_db(bob, bob.get_last_msg_id_in(msg1.chat_id).await).await?;
-            assert!(!no_info_msg.is_info());
-            assert_eq!(no_info_msg.text, "Bar");
+            assert!(unpin_msg.is_info());
+            assert!(!unpin_msg.hidden);
+            assert_eq!(unpin_msg.get_info_type(), SystemMessage::MessageUnpinned);
+            assert_eq!(unpin_msg.state, MessageState::InNoticed); // no notification, no badge
+            assert_eq!(bob.get_last_msg_id_in(msg1.chat_id).await, unpin_msg.id);
        }

        // Alice's second device receives all four messages and ends up in the same state
@@ -136,15 +135,11 @@ async fn test_pinned_messages() -> Result<()> {
        expect_pinned_message_event(alice2, msg1.chat_id).await;
        assert!(Message::load_from_db(alice2, msg1.id).await?.is_pinned());

-        alice2.recv_msg(&sent3).await;
-        alice2.recv_msg_trash(&sent4).await;
+        let unpin_msg = alice2.recv_msg(&sent3).await;
        expect_pinned_message_event(alice2, msg1.chat_id).await;
        assert!(!Message::load_from_db(alice2, msg1.id).await?.is_pinned());
-
-        let no_info_msg =
-            Message::load_from_db(alice2, alice2.get_last_msg_id_in(msg1.chat_id).await).await?;
-        assert!(!no_info_msg.is_info());
-        assert_eq!(no_info_msg.text, "Bar");
+        assert_eq!(unpin_msg.get_info_type(), SystemMessage::MessageUnpinned);
+        assert_eq!(unpin_msg.text, "You unpinned a message.");
    }

    Ok(())
@@ -156,14 +156,6 @@ mod tests {
        };
        assert!(!t.quota_needs_update(0, TIMEOUT).await);

-        t.evtracker.clear_events();
-        t.set_primary_self_addr("new@addr").await?;
-        assert!(t.quota.read().await.is_empty());
-        t.evtracker
-            .get_matching(|evt| matches!(evt, EventType::ConnectivityChanged))
-            .await;
-        assert!(t.quota_needs_update(0, TIMEOUT).await);
-
        Ok(())
    }
 }
@@ -354,9 +354,12 @@ pub(crate) fn refine_frequencies(
 mod tests {
    use super::*;
    use crate::chat::create_broadcast;
+    use crate::chatlist::Chatlist;
    use crate::reaction::send_reaction;
    use crate::securejoin::get_securejoin_qr;
-    use crate::test_utils::TestContextManager;
+    use crate::test_utils::{TestContextManager, sync};
+    use crate::tools::SystemTime;
+    use std::time::Duration;

    #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
    async fn test_broadcast_reaction_wire_format() {
@@ -583,6 +586,34 @@ mod tests {
        assert_eq!(result[1].is_from_self, true);
    }

+    #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+    async fn test_broadcast_reactions_not_in_chatlist_summary() -> Result<()> {
+        let mut tcm = TestContextManager::new();
+        let alice = &tcm.alice().await;
+        let bob = &tcm.bob().await;
+
+        let alice_chat_id = create_broadcast(alice, "Channel".to_string()).await?;
+        let qr = get_securejoin_qr(alice, Some(alice_chat_id)).await?;
+        let bob_chat_id = tcm.exec_securejoin_qr(bob, alice, &qr).await;
+        bob_chat_id.accept(bob).await?;
+
+        let sent_msg = alice.send_text(alice_chat_id, "hi channel!").await;
+        let bob_msg = bob.recv_msg(&sent_msg).await;
+
+        // reactions show up in the summary only if newer than the message; make sure that is the case.
+        SystemTime::shift(Duration::from_secs(10));
+
+        send_reaction(bob, bob_msg.id, "❤️").await?;
+        alice.recv_msg_hidden(&bob.pop_sent_msg().await).await;
+
+        for t in [alice, bob] {
+            let chatlist = Chatlist::try_load(t, 0, None, None).await?;
+            let summary = chatlist.get_summary(t, 0, None).await?;
+            assert_eq!(summary.text, "hi channel!");
+        }
+        Ok(())
+    }
+
    #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
    async fn test_broadcast_channel_reaction() -> Result<()> {
        let mut tcm = TestContextManager::new();
@@ -721,6 +752,67 @@ mod tests {
        Ok(())
    }

+    /// The channel owner has two devices.
+    /// A reaction summary sent by one device must not make the other device
+    /// broadcast the summary again, otherwise the devices send summaries to each other
+    /// (and to all subscribers) every `REACTION_BROADCAST_PERIOD` forever.
+    #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+    async fn test_broadcast_reactions_multidevice_no_loop() -> Result<()> {
+        let mut tcm = TestContextManager::new();
+        let alice1 = &tcm.alice().await;
+        let alice2 = &tcm.alice().await;
+        let bob = &tcm.bob().await;
+        for a in [alice1, alice2] {
+            a.set_config_bool(Config::SyncMsgs, true).await?;
+        }
+
+        let alice1_chat_id = create_broadcast(alice1, "Channel".to_string()).await?;
+        sync(alice1, alice2).await;
+        let qr = get_securejoin_qr(alice1, Some(alice1_chat_id)).await?;
+        let bob_chat_id = tcm.exec_securejoin_qr(bob, alice1, &qr).await;
+        bob_chat_id.accept(bob).await?;
+
+        tcm.section("Alice1 posts, Alice2 and Bob receive the post");
+        let sent_msg = alice1.send_text(alice1_chat_id, "hi channel!").await;
+        let alice1_msg_id = sent_msg.load_from_db().await.id;
+        let alice2_msg = alice2.recv_msg(&sent_msg).await;
+        let bob_msg = bob.recv_msg(&sent_msg).await;
+
+        tcm.section("Alice2 reacts to her own post, Alice1 learns about it");
+        send_reaction(alice2, alice2_msg.id, "👍").await?;
+        alice1.recv_msg_hidden(&alice2.pop_sent_msg().await).await;
+        assert_eq!(
+            get_msg_reactions(alice1, alice1_msg_id).await?.to_string(),
+            "👍1"
+        );
+        broadcast_reactions_for_all_chats(alice2).await?; // bypass timer
+        let summary = alice2.pop_sent_msg().await;
+        alice1.recv_msg_hidden(&summary).await;
+        bob.recv_msg_hidden(&summary).await;
+
+        tcm.section("Bob reacts, Alice1 broadcasts the summary");
+        send_reaction(bob, bob_msg.id, "❤️").await?;
+        alice1.recv_msg_hidden(&bob.pop_sent_msg().await).await;
+        broadcast_reactions_for_all_chats(alice1).await?; // bypass timer
+        let summary = alice1.pop_sent_msg().await;
+        bob.recv_msg_hidden(&summary).await;
+        assert_eq!(
+            get_msg_reactions(bob, bob_msg.id).await?.to_string(),
+            "❤️1 👍1"
+        );
+
+        tcm.section("Alice2 receives Alice1's summary and must not broadcast it again");
+        alice2.recv_msg_hidden(&summary).await;
+        broadcast_reactions_for_all_chats(alice2).await?;
+        assert!(alice2.pop_sent_msg_opt().await.is_none());
+
+        tcm.section("The summary must not remove Alice's own reaction on Alice2");
+        let reactions = get_msg_reactions(alice2, alice2_msg.id).await?;
+        assert_eq!(reactions.to_string(), "👍1");
+
+        Ok(())
+    }
+
    #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
    async fn test_broadcast_subscriber_sends_unallowed_reaction() -> Result<()> {
        let mut tcm = TestContextManager::new();
@@ -483,7 +483,12 @@ pub(crate) async fn receive_imf_inner(
    }

    let trash = || async {
-        let msg_ids = vec![insert_tombstone(context, rfc724_mid, false).await?];
+        let msg_ids = vec![
+            context
+                .sql
+                .transaction(|tx| insert_tombstone(tx, rfc724_mid, false))
+                .await?,
+        ];
        Ok(Some(ReceivedMsg {
            chat_id: ChatId::TRASH,
            state: MessageState::Undefined,
@@ -669,7 +674,10 @@ pub(crate) async fn receive_imf_inner(
        match res {
            securejoin::HandshakeMessage::Done | securejoin::HandshakeMessage::Ignore => {
                let needs_delete_job = res == securejoin::HandshakeMessage::Done;
-                let msg_id = insert_tombstone(context, rfc724_mid, needs_delete_job).await?;
+                let msg_id = context
+                    .sql
+                    .transaction(|tx| insert_tombstone(tx, rfc724_mid, needs_delete_job))
+                    .await?;
                received_msg = Some(ReceivedMsg {
                    chat_id: ChatId::TRASH,
                    state: MessageState::InSeen,
@@ -933,9 +941,15 @@ pub(crate) async fn receive_imf_inner(
                        warn!(context, "MDN: Not encrypted. Ignoring.");
                        continue;
                    }
-                    message::update_msg_state(context, msg_id, MessageState::InSeen).await?;
-                    if let Err(e) = msg_id.start_ephemeral_timer(context).await {
-                        error!(context, "start_ephemeral_timer for {msg_id}: {e:#}.");
+                    let trigger_ephemeral_interrupt = context
+                        .sql
+                        .transaction(|tx| {
+                            message::update_msg_state(tx, msg_id, MessageState::InSeen)?;
+                            msg_id.start_ephemeral_timer(tx)
+                        })
+                        .await?;
+                    if trigger_ephemeral_interrupt {
+                        context.scheduler.interrupt_ephemeral_task().await;
                    }
                    if !mime_parser.has_chat_version() {
                        continue;
@@ -1153,9 +1167,6 @@ async fn decide_chat_assignment(
    {
        info!(context, "Call state changed (TRASH).");
        true
-    } else if mime_parser.is_system_message == SystemMessage::MessageUnpinned {
-        info!(context, "Message unpinned (TRASH).");
-        true
    } else if let Some(ref decryption_error) = mime_parser.decryption_error
        && !mime_parser.incoming
    {
@@ -1828,13 +1839,17 @@ async fn add_parts(
        EphemeralTimer::Disabled
    };

+    // silent messages are added as "noticed" and do not bubble up in the chatlist
+    let silent =
+        group_changes.silent || mime_parser.is_system_message == SystemMessage::MessageUnpinned;
+
    let state = if !mime_parser.incoming {
        MessageState::OutDelivered
    } else if seen || !mime_parser.mdn_reports.is_empty() || chat_id_blocked == Blocked::Yes
    // No check for `hidden` because only reactions are such and they should be `InFresh`.
    {
        MessageState::InSeen
-    } else if mime_parser.from.addr == STATISTICS_BOT_EMAIL || group_changes.silent {
+    } else if mime_parser.from.addr == STATISTICS_BOT_EMAIL || silent {
        MessageState::InNoticed
    } else {
        MessageState::InFresh
@@ -1944,21 +1959,17 @@ async fn add_parts(

        Some(better_msg)
    } else if mime_parser.is_system_message == SystemMessage::MessagePinned {
-        Some(stock_str::msg_pinned(context, from_id).await) // message unpinned info is trashed in decide_chat_assignment()
+        Some(stock_str::msg_pinned(context, from_id).await)
+    } else if mime_parser.is_system_message == SystemMessage::MessageUnpinned {
+        Some(stock_str::msg_unpinned(context, from_id).await)
    } else {
        None
    };

    drop(chat); // Avoid using stale `chat` object.

-    let sort_timestamp = tweak_sort_timestamp(
-        context,
-        mime_parser,
-        group_changes.silent,
-        chat_id,
-        sort_timestamp,
-    )
-    .await?;
+    let sort_timestamp =
+        tweak_sort_timestamp(context, mime_parser, silent, chat_id, sort_timestamp).await?;

    let mime_in_reply_to = mime_parser
        .get_header(HeaderDef::InReplyTo)
@@ -2106,7 +2117,11 @@ async fn add_parts(
    let mut parts = mime_parser.parts.iter().peekable();
    while let Some(part) = parts.next() {
        let hidden = part.is_reaction;
-        if part.is_reaction {
+        // A reaction summary of a broadcast channel (`Chat-Broadcast-States:`) is sent as an empty
+        // reaction to the latest channel message, but it is not a reaction of the sender.
+        // Applying it would remove the owner's own reaction and, on another device of the owner,
+        // queue the message for the next summary, so the devices would resend summaries forever.
+        if part.is_reaction && mime_parser.broadcast_reactions.is_none() {
            let reaction_str = simplify::remove_footers(part.msg.as_str());
            let is_incoming_fresh =
                mime_parser.incoming && !seen && chat_id_blocked == Blocked::Not;
@@ -2402,7 +2417,10 @@ async fn handle_edit_delete(
            let Some(msg_id) = message::rfc724_mid_exists(context, rfc724_mid).await? else {
                warn!(context, "Delete message: {rfc724_mid:?} not found.");
                // Insert a tombstone so that the message will be ignored if it arrives later within a period specified in prune_tombstones().
-                insert_tombstone(context, rfc724_mid, false).await?;
+                context
+                    .sql
+                    .transaction(|tx| insert_tombstone(tx, rfc724_mid, false))
+                    .await?;
                continue;
            };

@@ -3853,7 +3853,7 @@ async fn test_unsigned_chat_group_hdr() -> Result<()> {
    let mut tcm = TestContextManager::new();
    let alice = &tcm.alice().await;
    let bob = &tcm.bob().await;
-    let bob_addr = bob.get_config(Config::ConfiguredAddr).await?.unwrap();
+    let bob_addr = bob.get_primary_self_addr().await?;
    let bob_id = alice.add_or_lookup_contact_id(bob).await;
    let alice_chat_id = create_group(alice, "foos").await?;
    add_contact_to_chat(alice, alice_chat_id, bob_id).await?;
@@ -4541,7 +4541,7 @@ async fn test_outgoing_msg_forgery() -> Result<()> {
    let mut tcm = TestContextManager::new();
    let export_dir = tempfile::tempdir().unwrap();
    let alice = &tcm.alice().await;
-    let alice_addr = &alice.get_config(Config::ConfiguredAddr).await?.unwrap();
+    let alice_addr = &alice.get_primary_self_addr().await?;
    imex(alice, ImexMode::ExportSelfKeys, export_dir.path(), None).await?;
    // We need Bob only to encrypt the forged message to Alice's key, actually Bob doesn't
    // participate in the scenario.
@@ -5638,7 +5638,7 @@ async fn test_bcc_not_a_group() -> Result<()> {
 async fn test_lookup_key_contact_by_address_self() -> Result<()> {
    let mut tcm = TestContextManager::new();
    let t = &tcm.alice().await;
-    let addr = &t.get_config(Config::ConfiguredAddr).await?.unwrap();
+    let addr = &t.get_primary_self_addr().await?;
    assert_eq!(
        lookup_key_contact_by_address(t, addr, None).await?,
        Some(ContactId::SELF)
@@ -5690,10 +5690,7 @@ async fn test_outgoing_determined_by_signature() -> Result<()> {
    let alice_dev2 = &tcm.unconfigured().await;
    alice_dev2.configure_addr(different_from).await;
    key::store_self_keypair(alice_dev2, &alice_keypair()).await?;
-    assert_ne!(
-        alice.get_config(Config::ConfiguredAddr).await?.unwrap(),
-        different_from
-    );
+    assert_ne!(alice.get_primary_self_addr().await?, different_from);

    // Send message from alice_dev2 and check alice sees it as outgoing
    let chat_id = alice_dev2.create_chat_id(bob).await;
@@ -4,9 +4,8 @@ use std::num::NonZeroUsize;
 use std::pin::Pin;
 use std::sync::atomic::Ordering;

-use anyhow::{Context as _, Error, Result, bail};
+use anyhow::{Context as _, Error, Result};
 use async_channel::{self as channel, Receiver, Sender};
-use futures::future::try_join_all;
 use futures_lite::FutureExt;
 use tokio::sync::{RwLock, oneshot};
 use tokio::task::{self, JoinSet};
@@ -319,7 +318,7 @@ impl SchedulerState {
        }

        while let Some(fetched) = set.join_next().await {
-            if let Ok(true) = fetched {
+            if fetched.context("background_fetch_any: Failed to join a task")? {
                break;
            }
        }
@@ -403,11 +402,7 @@ pub(crate) struct Scheduler {
    recently_seen_loop: RecentlySeenLoop,
 }

-async fn inbox_loop(
-    ctx: Context,
-    started: oneshot::Sender<()>,
-    inbox_handlers: ImapConnectionHandlers,
-) {
+async fn inbox_loop(ctx: Context, inbox_handlers: ImapConnectionHandlers) {
    use futures::future::FutureExt;

    info!(ctx, "Starting inbox loop.");
@@ -420,10 +415,6 @@ async fn inbox_loop(
    let ctx1 = ctx.clone();
    let fut = async move {
        let ctx = ctx1;
-        if let Err(()) = started.send(()) {
-            warn!(ctx, "Inbox loop, missing started receiver.");
-            return;
-        };

        let mut old_session: Option<Session> = None;
        loop {
@@ -611,11 +602,7 @@ async fn fetch_idle(ctx: &Context, connection: &mut Imap, mut session: Session)
    Ok(session)
 }

-async fn smtp_loop(
-    ctx: Context,
-    started: oneshot::Sender<()>,
-    smtp_handlers: SmtpConnectionHandlers,
-) {
+async fn smtp_loop(ctx: Context, smtp_handlers: SmtpConnectionHandlers) {
    use futures::future::FutureExt;

    info!(ctx, "Starting SMTP loop.");
@@ -628,10 +615,6 @@ async fn smtp_loop(
    let ctx1 = ctx.clone();
    let fut = async move {
        let ctx = ctx1;
-        if let Err(()) = started.send(()) {
-            warn!(&ctx, "SMTP loop, missing started receiver.");
-            return;
-        }

        // Reschedule the check to catch changes lost to a restart.
        schedule_keyupdate_check(&ctx).await.log_err(&ctx).ok();
@@ -678,11 +661,11 @@ async fn smtp_loop(
                    "SMTP has messages to retry, planning to retry {t} seconds later."
                );
                let duration = std::time::Duration::from_secs(t);
-                tokio::time::timeout(duration, async {
-                    idle_interrupt_receiver.recv().await.unwrap_or_default()
-                })
-                .await
-                .unwrap_or_default();
+                if let Ok(Err(async_channel::RecvError)) =
+                    tokio::time::timeout(duration, idle_interrupt_receiver.recv()).await
+                {
+                    break;
+                }
                let slept = time_elapsed(&now).as_secs();
                timeout = Some(cmp::max(
                    t,
@@ -706,11 +689,15 @@ async fn smtp_loop(
                info!(ctx, "SMTP has no messages to retry, waiting for interrupt.");
                let interrupt = idle_interrupt_receiver.recv();
                if next_check != 0 {
-                    tokio::time::timeout(std::time::Duration::from_secs(wait), interrupt)
-                        .await
-                        .ok();
+                    if let Ok(Err(async_channel::RecvError)) =
+                        tokio::time::timeout(std::time::Duration::from_secs(wait), interrupt).await
+                    {
+                        break;
+                    }
                } else {
-                    interrupt.await.ok();
+                    if let Err(async_channel::RecvError) = interrupt.await {
+                        break;
+                    }
                }
            };

@@ -732,20 +719,17 @@ impl Scheduler {
    pub async fn start(ctx: &Context) -> Result<Self> {
        let (smtp, smtp_handlers) = SmtpConnectionState::new();

-        let (smtp_start_send, smtp_start_recv) = oneshot::channel();
        let (ephemeral_interrupt_send, ephemeral_interrupt_recv) = channel::bounded(1);
        let (location_interrupt_send, location_interrupt_recv) = channel::bounded(1);

        let mut inboxes = Vec::new();
-        let mut start_recvs = Vec::new();

        for (transport_id, configured_login_param) in ConfiguredLoginParam::load_all(ctx).await? {
            let (conn_state, inbox_handlers) =
                ImapConnectionState::new(ctx, transport_id, configured_login_param.clone()).await?;
-            let (inbox_start_send, inbox_start_recv) = oneshot::channel();
            let handle = {
                let ctx = ctx.clone();
-                task::spawn(inbox_loop(ctx, inbox_start_send, inbox_handlers))
+                task::spawn(inbox_loop(ctx, inbox_handlers))
            };
            let addr = configured_login_param.addr.clone();
            let folder = configured_login_param
@@ -758,14 +742,12 @@ impl Scheduler {
                handle,
            };
            inboxes.push(inbox);
-            start_recvs.push(inbox_start_recv);
        }

        let smtp_handle = {
            let ctx = ctx.clone();
-            task::spawn(smtp_loop(ctx, smtp_start_send, smtp_handlers))
+            task::spawn(smtp_loop(ctx, smtp_handlers))
        };
-        start_recvs.push(smtp_start_recv);

        let ephemeral_handle = {
            let ctx = ctx.clone();
@@ -794,11 +776,6 @@ impl Scheduler {
            recently_seen_loop,
        };

-        // wait for all loops to be started
-        if let Err(err) = try_join_all(start_recvs).await {
-            bail!("failed to start scheduler: {err}");
-        }
-
        info!(ctx, "scheduler is running");
        Ok(res)
    }
@@ -851,20 +828,31 @@ impl Scheduler {
        let timeout_duration = std::time::Duration::from_secs(30);

        let tracker = TaskTracker::new();
-        for b in self.inboxes {
+        for mut b in self.inboxes {
            let context = context.clone();
            tracker.spawn(async move {
-                tokio::time::timeout(timeout_duration, b.handle)
+                if tokio::time::timeout(timeout_duration, &mut b.handle)
                    .await
-                    .log_err(&context)
+                    .is_err()
+                {
+                    warn!(context, "IMAP shutdown timed out; aborting task.");
+                    b.handle.abort();
+                    b.handle.await.ok();
+                }
            });
        }
        {
            let context = context.clone();
            tracker.spawn(async move {
-                tokio::time::timeout(timeout_duration, self.smtp_handle)
+                let mut handle = self.smtp_handle;
+                if tokio::time::timeout(timeout_duration, &mut handle)
                    .await
-                    .log_err(&context)
+                    .is_err()
+                {
+                    warn!(context, "SMTP shutdown timed out; aborting task.");
+                    handle.abort();
+                    handle.await.ok();
+                }
            });
        }
        tracker.close();
@@ -33,7 +33,7 @@ pub(crate) use qrinvite::QrInvite;

 use crate::token::Namespace;

-const DISALLOWED_CHARACTERS: &AsciiSet = &NON_ALPHANUMERIC_WITHOUT_DOT.remove(b'_').remove(b'@');
+const DISALLOWED_CHARACTERS: &AsciiSet = &NON_ALPHANUMERIC_WITHOUT_DOT.remove(b'_');

 fn inviter_progress(
    context: &Context,
@@ -543,7 +543,10 @@ pub(crate) async fn handle_securejoin_handshake(
            )
            .await?;

-            insert_into_smtp(context, &rfc724_mid, &queued_message).await?;
+            context
+                .sql
+                .transaction(|tx| insert_into_smtp(tx, &rfc724_mid, &queued_message))
+                .await?;
            context.scheduler.interrupt_smtp().await;

            Ok(HandshakeMessage::Done)
@@ -339,7 +339,10 @@ pub(crate) async fn send_handshake_message(
            recipients.to_vec(),
        )
        .await?;
-        insert_into_smtp(context, &rfc724_mid, &queued_msg).await?;
+        context
+            .sql
+            .transaction(|tx| insert_into_smtp(tx, &rfc724_mid, &queued_msg))
+            .await?;

        context.scheduler.interrupt_smtp().await;
    } else {
@@ -50,11 +50,7 @@ async fn test_setup_contact_ext(case: SetupContactCase) -> (TestContext, TestCon

    let mut tcm = TestContextManager::new();
    let alice = tcm.alice().await;
-    let alice_addr = &alice
-        .get_config(Config::ConfiguredAddr)
-        .await
-        .unwrap()
-        .unwrap();
+    let alice_addr = alice.get_primary_self_addr().await.unwrap();
    if case == SetupContactCase::AliceHasName {
        alice
            .set_config(Config::Displayname, Some("Alice"))
@@ -118,7 +114,7 @@ async fn test_setup_contact_ext(case: SetupContactCase) -> (TestContext, TestCon
    let contact_alice_id = bob.add_or_lookup_contact_no_key(&alice).await.id;
    let sent = bob.pop_sent_msg().await;
    assert!(!sent.payload.contains("Bob Examplenet"));
-    assert_eq!(sent.recipient(), EmailAddress::new(alice_addr).unwrap());
+    assert_eq!(sent.recipients, *alice_addr);
    let msg = alice.parse_msg(&sent).await;
    assert!(msg.signature.is_none());
    assert_eq!(
@@ -1160,12 +1156,12 @@ async fn test_get_securejoin_qr_encoding() -> Result<()> {

    let qr = get_securejoin_qr(alice, None).await?;
    assert!(
-        qr.contains("a=jk%25l@example.net"),
-        "{qr} doesn't contain 'a=jk%25l@example.net'"
+        qr.contains("a=jk%25l%40example.net"),
+        "{qr} doesn't contain 'a=jk%25l%40example.net'"
    );
    assert!(
-        qr.contains("r=asdf@example.org,alice@example.org"),
-        "{qr} doesn't contain 'r=asdf@example.org,alice@example.org'"
+        qr.contains("r=asdf%40example.org,alice%40example.org"),
+        "{qr} doesn't contain 'r=asdf%40example.org,alice%40example.org'"
    );

    let qr = check_qr(bob, &qr).await?;
@@ -13,7 +13,6 @@ use rusqlite::OptionalExtension as _;
 use tokio::task;

 use crate::chat::{ChatId, add_info_msg_with_cmd};
-use crate::config::Config;
 use crate::contact::{Contact, ContactId};
 use crate::context::Context;
 use crate::events::EventType;
@@ -32,21 +31,26 @@ use crate::transport::{
    ConfiguredLoginParam, ConfiguredServerLoginParam, prioritize_server_login_params,
 };

+/// SMTP connection with information about it.
+#[derive(Debug)]
+struct Connection {
+    transport: SmtpTransport<Box<dyn SessionBufStream>>,
+
+    /// Email address that should be put into the From field when sending over this connection.
+    from: EmailAddress,
+
+    /// ID of the transport from which SMTP connection configuration comes from.
+    transport_id: u32,
+
+    /// Timestamp of last successful send/receive network interaction
+    /// (eg connect or send succeeded).
+    last_success: tools::Time,
+}
+
 #[derive(Default)]
 pub(crate) struct Smtp {
    /// SMTP connection.
-    transport: Option<SmtpTransport<Box<dyn SessionBufStream>>>,
-
-    /// Email address we are sending from.
-    from: Option<EmailAddress>,
-
-    /// Transport we are connected to.
-    transport_id: Option<u32>,
-
-    /// Timestamp of last successful send/receive network interaction
-    /// (eg connect or send succeeded). On initialization and disconnect
-    /// it is set to None.
-    last_success: Option<tools::Time>,
+    connection: Option<Connection>,

    pub(crate) connectivity: ConnectivityStore,

@@ -61,7 +65,10 @@ async fn sorted_transports(context: &Context) -> Result<Vec<(u32, ConfiguredLogi
        .query_map_vec(
            "SELECT transports.id, configured_param FROM transports
             LEFT JOIN smtp_success ON smtp_success.transport_id=transports.id
-             ORDER BY IFNULL(smtp_success.id, 0) DESC, transports.id ASC",
+             LEFT JOIN smtp_failure ON smtp_failure.transport_id=transports.id
+             ORDER BY IFNULL(smtp_success.id, 0) DESC,
+                      IFNULL(smtp_failure.id, 0) ASC,
+                      transports.id ASC",
            (),
            |row| {
                let id: u32 = row.get(0)?;
@@ -79,10 +86,37 @@ async fn record_success(context: &Context, transport_id: u32) -> Result<()> {
    // if the row exists already, so it becomes the highest rowid in the table.
    context
        .sql
-        .execute(
-            "INSERT OR REPLACE INTO smtp_success (transport_id) VALUES (?)",
-            (transport_id,),
-        )
+        .transaction(|t| {
+            t.execute(
+                "INSERT OR REPLACE INTO smtp_success (transport_id) VALUES (?)",
+                (transport_id,),
+            )?;
+            t.execute(
+                "DELETE FROM smtp_failure WHERE transport_id = ?",
+                (transport_id,),
+            )?;
+            Ok(())
+        })
+        .await?;
+    Ok(())
+}
+
+/// Records a failure and removes last remembered success for
+/// SMTP transport so another transport is tried next time.
+async fn record_failure(context: &Context, transport_id: u32) -> Result<()> {
+    context
+        .sql
+        .transaction(|t| {
+            t.execute(
+                "INSERT OR REPLACE INTO smtp_failure (transport_id) VALUES (?)",
+                (transport_id,),
+            )?;
+            t.execute(
+                "DELETE FROM smtp_success WHERE transport_id = ?",
+                (transport_id,),
+            )?;
+            Ok(())
+        })
        .await?;
    Ok(())
 }
@@ -95,30 +129,25 @@ impl Smtp {

    /// Disconnect the SMTP transport and drop it entirely.
    pub fn disconnect(&mut self) {
-        if let Some(mut transport) = self.transport.take() {
+        if let Some(mut connection) = self.connection.take() {
            // Closing connection with a QUIT command may take some time, especially if it's a
            // stale connection and an attempt to send the command times out. Send a command in a
            // separate task to avoid waiting for reply or timeout.
-            task::spawn(async move { transport.quit().await });
+            task::spawn(async move { connection.transport.quit().await });
        }
-        self.transport_id = None;
-        self.from = None;
-        self.last_success = None;
    }

    /// Return true if smtp was connected but is not known to
    /// have been successfully used the last 60 seconds
    pub fn has_maybe_stale_connection(&self) -> bool {
-        if let Some(last_success) = self.last_success {
-            time_elapsed(&last_success).as_secs() > 60
-        } else {
-            false
-        }
+        self.connection
+            .as_ref()
+            .is_some_and(|connection| time_elapsed(&connection.last_success).as_secs() > 60)
    }

    /// Check whether we are connected.
    pub fn is_connected(&self) -> bool {
-        self.transport.is_some()
+        self.connection.is_some()
    }

    /// Connect using configured parameters.
@@ -143,14 +172,12 @@ impl Smtp {
                    &lp.smtp_password,
                    &proxy_config,
                    &lp.addr,
+                    transport_id,
                    lp.strict_tls(proxy_config.is_some())?,
                )
                .await
            {
-                Ok(()) => {
-                    self.transport_id = Some(transport_id);
-                    return Ok(());
-                }
+                Ok(()) => return Ok(()),
                Err(err) => {
                    warn!(
                        context,
@@ -163,6 +190,7 @@ impl Smtp {
    }

    /// Connect using the provided login params.
+    #[expect(clippy::too_many_arguments)]
    pub async fn connect(
        &mut self,
        context: &Context,
@@ -170,6 +198,7 @@ impl Smtp {
        password: &str,
        proxy_config: &Option<ProxyConfig>,
        addr: &str,
+        transport_id: u32,
        strict_tls: bool,
    ) -> Result<()> {
        if self.is_connected() {
@@ -179,7 +208,6 @@ impl Smtp {

        let from = EmailAddress::new(addr.to_string())
            .with_context(|| format!("Invalid address {addr:?}"))?;
-        self.from = Some(from);

        let login_params =
            prioritize_server_login_params(&context.sql, login_params, "smtp").await?;
@@ -204,8 +232,12 @@ impl Smtp {
                }
            };

-            self.transport = Some(transport);
-            self.last_success = Some(tools::Time::now());
+            self.connection = Some(Connection {
+                transport,
+                from,
+                transport_id,
+                last_success: tools::Time::now(),
+            });

            context.emit_event(EventType::SmtpConnected(format!(
                "SMTP-LOGIN as {} ok",
@@ -230,7 +262,7 @@ pub(crate) enum SendResult {
 }

 /// Tries to send a message.
-pub(crate) async fn smtp_send(
+async fn smtp_send(
    context: &Context,
    recipients: &[async_smtp::EmailAddress],
    message: &str,
@@ -246,14 +278,37 @@ pub(crate) async fn smtp_send(

    smtp.connectivity.set_working(context);

-    let send_result = smtp.send(context, recipients, message.as_bytes()).await;
-    smtp.last_send_error = send_result.as_ref().err().map(|e| e.to_string());
+    let Some(ref mut connection) = smtp.connection else {
+        warn!(
+            context,
+            "Failed to send a message because SMTP client is not connected."
+        );
+        return SendResult::Retry;
+    };
+    let transport_id = connection.transport_id;
+
+    let send_result = connection
+        .send(context, recipients, message.as_bytes())
+        .await;
+    smtp.last_send_error = send_result.as_ref().err().map(|e| format!("{e:#}"));

    let status = match send_result {
-        Err(crate::smtp::send::Error::SmtpSend(err)) => {
+        Err(send::Error::SmtpSend(err)) => {
            // Remote error, retry later.
            info!(context, "SMTP failed to send: {:?}.", &err);

+            // Record failure on any error returned by the server, but not network errors.
+            if matches!(
+                err,
+                async_smtp::error::Error::Permanent(_) | async_smtp::error::Error::Transient(_)
+            ) && let Err(err) = record_failure(context, transport_id).await
+            {
+                warn!(
+                    context,
+                    "Failed to remove success for {transport_id}: {err:#}."
+                )
+            }
+
            let res = match err {
                async_smtp::error::Error::Permanent(ref response) => {
                    // Workaround for incorrectly configured servers returning permanent errors
@@ -327,44 +382,28 @@ pub(crate) async fn smtp_send(
                }
            };

-            // this clears last_success info
            info!(context, "Failed to send message over SMTP, disconnecting.");
            smtp.disconnect();

            res
        }
-        Err(crate::smtp::send::Error::Envelope(err)) => {
-            // Local error, job is invalid, do not retry.
-            smtp.disconnect();
-            warn!(context, "SMTP job is invalid: {err:#}.");
-            SendResult::Failure(err)
-        }
-        Err(crate::smtp::send::Error::NoTransport) => {
-            // Should never happen.
-            // It does not even make sense to disconnect here.
-            error!(context, "SMTP job failed because SMTP has no transport.");
-            SendResult::Failure(format_err!("SMTP has not transport"))
-        }
-        Err(crate::smtp::send::Error::Other(err)) => {
+        Err(send::Error::Other(err)) => {
            // Local error, job is invalid, do not retry.
            smtp.disconnect();
            warn!(context, "Unable to load SMTP job: {err:#}.");
            SendResult::Failure(err)
        }
-        Ok(()) => SendResult::Success,
-    };
-
-    if matches!(status, SendResult::Success) {
-        debug_assert!(smtp.transport_id.is_some());
-        if let Some(transport_id) = smtp.transport_id
-            && let Err(err) = record_success(context, transport_id).await
-        {
-            warn!(
-                context,
-                "Failed to record successful use of transport {transport_id} in smtp_success table: {err:#}."
-            );
+        Ok(()) => {
+            record_success(context, transport_id)
+                .await
+                .with_context(|| {
+                    format!("Failed to record successful use of transport {transport_id}")
+                })
+                .log_err(context)
+                .ok();
+            SendResult::Success
        }
-    }
+    };

    if let SendResult::Failure(err) = &status
        && let Some(msg_id) = msg_id
@@ -390,28 +429,21 @@ pub(crate) async fn smtp_send(

 /// Inserts a tombstone for `rfc724_mid`
 /// and queues the message for SMTP sending.
-pub(crate) async fn insert_into_smtp(
-    context: &Context,
+pub(crate) fn insert_into_smtp(
+    tx: &mut rusqlite::Transaction<'_>,
    rfc724_mid: &str,
    queued_msg: &QueuedMail,
 ) -> Result<()> {
    let now = tools::time();
-    let msg_id = message::insert_tombstone(context, rfc724_mid, false).await?;
-    context
-        .sql
-        .transaction(|transaction| queue::enqueue_mail(transaction, now, msg_id, queued_msg, None))
-        .await?;
+    let msg_id = message::insert_tombstone(tx, rfc724_mid, false)?;
+    queue::enqueue_mail(tx, now, msg_id, queued_msg, None)?;
    Ok(())
 }

 /// Sends message identified by `smtp` table rowid over SMTP connection.
 ///
 /// Removes row if the message should not be retried, otherwise increments retry count.
-pub(crate) async fn send_msg_to_smtp(
-    context: &Context,
-    smtp: &mut Smtp,
-    rowid: i64,
-) -> anyhow::Result<()> {
+pub(crate) async fn send_msg_to_smtp(context: &Context, smtp: &mut Smtp, rowid: i64) -> Result<()> {
    if let Err(err) = smtp
        .connect_configured(context)
        .await
@@ -472,9 +504,10 @@ pub(crate) async fn send_msg_to_smtp(
    let mut recipients = queued_mail.recipients.clone();
    if queued_mail.bcc_self {
        let from_addr = smtp
-            .from
+            .connection
            .as_ref()
-            .context("No From address available, likely not connected")?
+            .context("Not connected")?
+            .from
            .to_string();
        add_self_recipients(
            context,
@@ -504,19 +537,24 @@ pub(crate) async fn send_msg_to_smtp(
    let public_key = key::load_self_public_key(context).await?;
    let secret_key = key::load_self_secret_key(context).await?;
    let from_addr = smtp
-        .from
+        .connection
        .as_ref()
-        .context("No From address available, likely not connected")?
+        .context("Not connected")?
+        .from
        .to_string();

-    let transport_id = smtp.transport_id.context("Not connected")?;
+    let transport_id = smtp
+        .connection
+        .as_ref()
+        .context("Not connected")?
+        .transport_id;
    let chunk_size = context
        .get_max_smtp_rcpt_to(transport_id, &from_addr)
        .await?
        .max(1);

    let rendered_mail =
-        mimefactory::render_queued_mail(queued_mail, &public_key, &secret_key, from_addr)?;
+        mimefactory::render_queued_mail(queued_mail, &public_key, &secret_key, from_addr.clone())?;
    let body = rendered_mail.message;

    info!(
@@ -587,15 +625,9 @@ pub(crate) async fn send_msg_to_smtp(
                    .await?;

                if let Some((chat_id, timestamp_sort)) = res {
-                    let addr = context.get_config(Config::ConfiguredAddr).await?;
-                    let text = unencrypted_email(
-                        context,
-                        addr.unwrap_or_default()
-                            .split('@')
-                            .nth(1)
-                            .unwrap_or_default(),
-                    )
-                    .await;
+                    let text =
+                        unencrypted_email(context, from_addr.split('@').nth(1).unwrap_or_default())
+                            .await;
                    add_info_msg_with_cmd(
                        context,
                        chat_id,
@@ -760,9 +792,10 @@ async fn send_mdn_rfc724_mid(
    let public_key = key::load_self_public_key(context).await?;
    let secret_key = key::load_self_secret_key(context).await?;
    let from = smtp
-        .from
+        .connection
        .as_ref()
-        .context("No From address, not connected")?
+        .context("Not connected")?
+        .from
        .to_string();
    let rendered_msg =
        mimefactory::render_queued_mail(queued_mdn, &public_key, &secret_key, from.clone())?;
@@ -780,7 +813,10 @@ async fn send_mdn_rfc724_mid(
                .ok()
        })
        .collect();
-    message::insert_tombstone(context, &rendered_msg.rfc724_mid, false).await?;
+    context
+        .sql
+        .transaction(|tx| message::insert_tombstone(tx, &rendered_msg.rfc724_mid, false))
+        .await?;
    match smtp_send(context, &recipients, &body, smtp, None).await {
        SendResult::Success => {
            if !recipients.is_empty() {
@@ -1,31 +1,27 @@
 //! # SMTP message sending

+use anyhow::Context as _;
 use async_smtp::{EmailAddress, Envelope, SendableEmail};

-use super::Smtp;
+use super::Connection;
 use crate::config::Config;
 use crate::context::Context;
-use crate::log::warn;
 use crate::tools;

 pub type Result<T> = std::result::Result<T, Error>;

 #[derive(Debug, thiserror::Error)]
 pub enum Error {
-    #[error("Envelope error: {}", _0)]
-    Envelope(anyhow::Error),
    #[error("Send error: {}", _0)]
    SmtpSend(async_smtp::error::Error),
-    #[error("SMTP has no transport")]
-    NoTransport,
-    #[error("{}", _0)]
+    #[error("{:#}", _0)]
    Other(#[from] anyhow::Error),
 }

-impl Smtp {
+impl Connection {
    /// Send a prepared mail to recipients.
    /// On successful send out Ok() is returned.
-    pub async fn send(
+    pub(super) async fn send(
        &mut self,
        context: &Context,
        recipients: &[EmailAddress],
@@ -38,21 +34,13 @@ impl Smtp {
            context.ratelimit.write().await.send();
        }

-        let envelope =
-            Envelope::new(self.from.clone(), recipients.to_vec()).map_err(Error::Envelope)?;
+        let envelope = Envelope::new(Some(self.from.clone()), recipients.to_vec())
+            .context("Envelope error")?;
        let mail = SendableEmail::new(envelope, message);

-        let Some(ref mut transport) = self.transport else {
-            warn!(
-                context,
-                "Failed to send a message because SMTP client has no SmtpTransport."
-            );
-            return Err(Error::NoTransport);
-        };
+        self.transport.send(mail).await.map_err(Error::SmtpSend)?;

-        transport.send(mail).await.map_err(Error::SmtpSend)?;
-
-        self.last_success = Some(tools::Time::now());
+        self.last_success = tools::Time::now();
        Ok(())
    }
 }
@@ -1,8 +1,25 @@
 use anyhow::Result;

-use crate::test_utils::TestContextManager;
+use crate::test_utils::{TestContext, TestContextManager};
 use crate::transport;

+async fn sorted_transport_addrs(t: &TestContext) -> Result<String> {
+    let transports = super::sorted_transports(t).await?;
+    let addrs: Vec<String> = transports
+        .into_iter()
+        .map(|(_transport_id, transport)| transport.addr)
+        .collect();
+    Ok(addrs.join(" "))
+}
+
+async fn sorted_transport_ids(t: &TestContext) -> Result<Vec<u32>> {
+    let transports = super::sorted_transports(t).await?;
+    Ok(transports
+        .into_iter()
+        .map(|(transport_id, _transport)| transport_id)
+        .collect())
+}
+
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn test_smtp_candidates() -> Result<()> {
    let mut tcm = TestContextManager::new();
@@ -12,38 +29,42 @@ async fn test_smtp_candidates() -> Result<()> {
    transport::add_pseudo_transport(t, "bar@example.net").await?;
    transport::add_pseudo_transport(t, "baz@example.net").await?;

-    let transports = super::sorted_transports(t).await?;
-    let [
-        (transport_id1, ref transport1),
-        (transport_id2, ref transport2),
-        (transport_id3, ref transport3),
-    ] = transports[..]
-    else {
-        panic!("Unexpected number of transports");
-    };
-
    // By default first added transport is used first.
-    assert_eq!(transport1.addr, "foo@example.net");
-    assert_eq!(transport2.addr, "bar@example.net");
-    assert_eq!(transport3.addr, "baz@example.net");
+    assert_eq!(
+        sorted_transport_addrs(t).await?,
+        "foo@example.net bar@example.net baz@example.net"
+    );
+    assert_eq!(sorted_transport_ids(t).await?, [1, 2, 3]);

-    super::record_success(t, transport_id3).await?;
-    let transports2 = super::sorted_transports(t).await?;
-    assert_eq!(transports2[0].0, transport_id3);
-    assert_eq!(transports2[1].0, transport_id1);
-    assert_eq!(transports2[2].0, transport_id2);
+    super::record_success(t, 3).await?;
+    assert_eq!(sorted_transport_ids(t).await?, [3, 1, 2]);

-    super::record_success(t, transport_id2).await?;
-    let transports3 = super::sorted_transports(t).await?;
-    assert_eq!(transports3[0].0, transport_id2);
-    assert_eq!(transports3[1].0, transport_id3);
-    assert_eq!(transports3[2].0, transport_id1);
+    super::record_success(t, 2).await?;
+    assert_eq!(sorted_transport_ids(t).await?, [2, 3, 1]);

-    super::record_success(t, transport_id3).await?;
-    let transports4 = super::sorted_transports(t).await?;
-    assert_eq!(transports4[0].0, transport_id3);
-    assert_eq!(transports4[1].0, transport_id2);
-    assert_eq!(transports4[2].0, transport_id1);
+    super::record_success(t, 3).await?;
+    assert_eq!(sorted_transport_ids(t).await?, [3, 2, 1]);
+
+    super::record_failure(t, 3).await?;
+    assert_eq!(sorted_transport_ids(t).await?, [2, 1, 3]);
+
+    // New transport is added before all failing transports.
+    transport::add_pseudo_transport(t, "qux@example.net").await?;
+    assert_eq!(
+        sorted_transport_addrs(t).await?,
+        "bar@example.net foo@example.net qux@example.net baz@example.net"
+    );
+    assert_eq!(sorted_transport_ids(t).await?, [2, 1, 4, 3]);
+
+    super::record_success(t, 4).await?;
+    assert_eq!(sorted_transport_ids(t).await?, [4, 2, 1, 3]);
+
+    super::record_failure(t, 4).await?;
+    assert_eq!(sorted_transport_ids(t).await?, [2, 1, 3, 4]);
+    super::record_failure(t, 3).await?;
+    assert_eq!(sorted_transport_ids(t).await?, [2, 1, 4, 3]);
+    super::record_failure(t, 2).await?;
+    assert_eq!(sorted_transport_ids(t).await?, [1, 4, 3, 2]);

    Ok(())
 }
@@ -2687,6 +2687,32 @@ CREATE TABLE smtp_success (
        .await?;
    }

+    inc_and_check(&mut migration_version, 169)?;
+    if dbversion < migration_version {
+        sql.execute_migration(
+            "
+CREATE TABLE smtp_failure (
+    id INTEGER PRIMARY KEY AUTOINCREMENT NOT NULL,
+    transport_id INTEGER UNIQUE NOT NULL,
+    FOREIGN KEY(transport_id) REFERENCES transports(id) ON DELETE CASCADE
+) STRICT;
+",
+            migration_version,
+        )
+        .await?;
+    }
+
+    inc_and_check(&mut migration_version, 170)?;
+    if dbversion < migration_version {
+        // Lets `delete_messages()` find rows marked for deletion without reading the folder's rows.
+        sql.execute_migration(
+            "CREATE INDEX IF NOT EXISTS imap_pending_deletions
+             ON imap(transport_id, folder) WHERE target != folder",
+            migration_version,
+        )
+        .await?;
+    }
+
    let new_version = sql
        .get_raw_config_int(VERSION_CFG)
        .await?
@@ -431,6 +431,12 @@ https://delta.chat/donate"))]

    #[strum(props(fallback = "Message pinned by %1$s."))]
    MsgMessagePinnedBy = 244,
+
+    #[strum(props(fallback = "You unpinned a message."))]
+    MsgYouUnpinnedAMessage = 246,
+
+    #[strum(props(fallback = "Message unpinned by %1$s."))]
+    MsgMessageUnpinnedBy = 247,
 }

 impl StockMessage {
@@ -617,7 +623,6 @@ pub(crate) async fn msg_chat_description_changed(
 }

 /// Stock strings for pinning a message; used in info messages, once tapped, UI scrolled to the pinned message.
-/// For unpinning a message, we do not add a visible info message as this is of fewer interest.
 pub(crate) async fn msg_pinned(context: &Context, by_contact: ContactId) -> String {
    if by_contact == ContactId::SELF {
        translated(context, StockMessage::MsgYouPinnedAMessage)
@@ -627,6 +632,17 @@ pub(crate) async fn msg_pinned(context: &Context, by_contact: ContactId) -> Stri
    }
 }

+/// Stock strings for unpinning a message; used in info messages, once tapped, UI scrolled to the unpinned message.
+/// Unpinning messages are not notified, but still shown in the chat as otherwise the last message may read "USER pinned a message", but nothing is pinned.
+pub(crate) async fn msg_unpinned(context: &Context, by_contact: ContactId) -> String {
+    if by_contact == ContactId::SELF {
+        translated(context, StockMessage::MsgYouUnpinnedAMessage)
+    } else {
+        translated(context, StockMessage::MsgMessageUnpinnedBy)
+            .replace1(&by_contact.get_stock_name(context).await)
+    }
+}
+
 /// Stock string, one of:
 /// - `Member %1$s added.`,
 /// - `You added member %1$s.`,
@@ -7,7 +7,7 @@ use std::str;
 use anyhow::Result;
 use num_traits::FromPrimitive;

-use crate::calls::{CallState, call_state};
+use crate::calls::CallState;
 use crate::chat::Chat;
 use crate::constants::Chattype;
 use crate::constants::DC_DESIRED_TEXT_LEN;
@@ -68,9 +68,11 @@ impl Summary {
        chat: &Chat,
        contact: Option<&Contact>,
    ) -> Result<Summary> {
-        if let Some((reaction_msg, reaction_contact_id, reaction)) = chat
-            .get_last_reaction_if_newer_than(context, msg.timestamp_sort)
-            .await?
+        let is_broadcast = matches!(chat.typ, Chattype::InBroadcast | Chattype::OutBroadcast);
+        if !is_broadcast
+            && let Some((reaction_msg, reaction_contact_id, reaction)) = chat
+                .get_last_reaction_if_newer_than(context, msg.timestamp_sort)
+                .await?
        {
            // there is a reaction newer than the latest message, show that.
            // sorting and therefore date is still the one of the last message,
@@ -237,11 +239,11 @@ impl Message {
                append_text = true;
            }
            Viewtype::Call => {
-                let call_info = context.load_call_by_id(self.id).await.unwrap_or(None);
-                let has_video = call_info.is_some_and(|c| c.has_video_initially());
-                let call_state = call_state(context, self.id)
-                    .await
-                    .unwrap_or(CallState::Alerting);
+                let call_info = context.load_call_by_message(self.clone());
+                let has_video = call_info.as_ref().is_some_and(|c| c.has_video_initially());
+                let call_state = call_info
+                    .as_ref()
+                    .map_or(CallState::Alerting, |c| c.call_state());
                emoji = Some(if has_video { "🎥" } else { "📞" });
                type_name = Some(match call_state {
                    CallState::Alerting | CallState::Active | CallState::Completed { .. } => {
@@ -193,21 +193,11 @@ impl TestContextManager {
        to.recv_msg(&sent).await
    }

-    pub async fn change_addr(&self, test_context: &TestContext, new_addr: &str) {
-        self.section(&format!(
-            "{} changes her self address and reconfigures",
-            test_context.name()
-        ));
-
+    pub async fn change_addr(&self, test_context: &mut TestContext, new_addr: &str) {
        test_context.add_transport(new_addr).await;
-        test_context.set_primary_self_addr(new_addr).await.unwrap();
+        test_context.set_sending_addr(new_addr).await;
        // ensure_secret_key_exists() is called during configure
        key::ensure_secret_key_exists(test_context).await.unwrap();
-
-        assert_eq!(
-            test_context.get_primary_self_addr().await.unwrap(),
-            new_addr
-        );
    }

    /// Executes SecureJoin protocol between `scanner` and `scanned`.
@@ -252,10 +242,9 @@ impl TestContextManager {
        qr: &str,
    ) -> ChatId {
        assert!(joiner.pop_sent_msg_opt().await.is_none());
-        let inviter_addr = inviters[0].get_primary_self_addr().await.unwrap();
+        let inviter_addr = inviters[0].sending_addr().await;
        for inviter in inviters {
            assert!(inviter.pop_sent_msg_opt().await.is_none());
-            assert_eq!(inviter.get_primary_self_addr().await.unwrap(), inviter_addr);
        }

        let chat_id = join_securejoin(&joiner.ctx, qr).await.unwrap();
@@ -435,6 +424,9 @@ pub struct TestContext {
    pub evtracker: EventTracker,

    log_sink: LogSink,
+
+    /// From address to be used when emulating sending.
+    from_for_test_msgs: Option<String>,
 }

 impl TestContext {
@@ -530,6 +522,7 @@ impl TestContext {
            dir,
            evtracker: EventTracker::new(evtracker_receiver),
            log_sink,
+            from_for_test_msgs: None,
        }
    }

@@ -560,10 +553,6 @@ impl TestContext {
        add_pseudo_transport(&self.ctx, addr)
            .await
            .expect("Failed to add pseudo transport");
-        self.ctx
-            .set_config(Config::ConfiguredAddr, Some(addr))
-            .await
-            .expect("Failed to configure address");

        if let Some(name) = addr.split('@').next() {
            self.set_name(name);
@@ -586,6 +575,28 @@ impl TestContext {
        self.self_public_key.lock().await.take();
    }

+    pub async fn set_sending_addr(&mut self, addr: &str) {
+        if !self
+            .sql
+            .exists("SELECT COUNT(*) FROM transports WHERE addr=?", (addr,))
+            .await
+            .unwrap()
+        {
+            panic!("Address {addr} is not configured");
+        }
+        self.from_for_test_msgs = Some(addr.to_string());
+    }
+
+    pub async fn sending_addr(&self) -> String {
+        if let Some(ref from) = self.from_for_test_msgs {
+            from.clone()
+        } else {
+            self.get_primary_self_addr()
+                .await
+                .expect("Cannot get From address")
+        }
+    }
+
    /// Retrieves a sent message from the jobs table.
    ///
    /// This retrieves and removes a message which has been scheduled to send from the jobs
@@ -632,10 +643,7 @@ ORDER BY id"
            .await
            .expect("Failed to load queued mail");
        if queued_mail.bcc_self {
-            let from = self
-                .get_primary_self_addr()
-                .await
-                .expect("Cannot get From address");
+            let from = self.sending_addr().await;
            smtp::add_self_recipients(
                &self.ctx,
                &mut queued_mail.recipients,
@@ -734,10 +742,7 @@ ORDER BY id"
                .await
                .expect("Failed to load queued mail");
            if queued_mail.bcc_self {
-                let from = self
-                    .get_primary_self_addr()
-                    .await
-                    .expect("Cannot get self address");
+                let from = self.sending_addr().await;
                smtp::add_self_recipients(
                    &self.ctx,
                    &mut queued_mail.recipients,
@@ -895,9 +900,23 @@ ORDER BY id"
            .expect("failed to load msg")
    }

+    /// Returns the `EXPLAIN QUERY PLAN` steps of `query`.
+    pub async fn query_plan(&self, query: &str) -> Result<Vec<String>> {
+        self.sql
+            .call(true, |conn| {
+                let mut stmt = conn.prepare(&format!("EXPLAIN QUERY PLAN {query}"))?;
+                let plan = stmt
+                    .raw_query()
+                    .mapped(|row| row.get::<_, String>(3))
+                    .collect::<rusqlite::Result<Vec<_>>>()?;
+                Ok(plan)
+            })
+            .await
+    }
+
    /// Returns the [`ContactId`] for the other [`TestContext`], creating a contact if necessary.
    pub async fn add_or_lookup_address_contact_id(&self, other: &TestContext) -> ContactId {
-        let primary_self_addr = other.ctx.get_primary_self_addr().await.unwrap();
+        let primary_self_addr = other.sending_addr().await;
        let addr = ContactAddress::new(&primary_self_addr).unwrap();
        // MailinglistAddress is the lowest allowed origin, we'd prefer to not modify the
        // origin when creating this contact.
@@ -952,7 +971,7 @@ ORDER BY id"
    /// If the contact does not exist yet, a new contact will be created
    /// with the correct fingerprint, but without the public key.
    pub async fn add_or_lookup_contact_id_no_key(&self, other: &TestContext) -> ContactId {
-        let primary_self_addr = other.ctx.get_primary_self_addr().await.unwrap();
+        let primary_self_addr = other.sending_addr().await;
        let addr = ContactAddress::new(&primary_self_addr).unwrap();
        let fingerprint = self_fingerprint(other).await.unwrap();

@@ -1242,13 +1261,14 @@ ORDER BY id"
 }

 pub async fn encrypt_raw_message(
-    context: &Context,
+    context: &TestContext,
    receivers: &[&TestContext],
    payload: &[u8],
 ) -> Result<String> {
    let public_key = key::load_self_public_key(context).await?;
+    let from = context.sending_addr().await;
    let aheader = Aheader {
-        addr: context.get_primary_self_addr().await?,
+        addr: from.clone(),
        public_key: public_key.clone(),
        prefer_encrypt: EncryptPreference::Mutual,
    };
@@ -1259,7 +1279,6 @@ pub async fn encrypt_raw_message(
        encryption_keyring.push(key::load_self_public_key(receiver).await?);
    }

-    let from = context.get_primary_self_addr().await?;
    let compress = false;

    let mut cleartext = format!("Autocrypt: {aheader}").into_bytes();
@@ -20,13 +20,14 @@ use crate::test_utils::TestContextManager;
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn test_change_primary_self_addr() -> Result<()> {
    let mut tcm = TestContextManager::new();
-    let alice = tcm.alice().await;
+    let mut alice = tcm.alice().await;
    let bob = tcm.bob().await;

    tcm.send_recv_accept(&alice, &bob, "Hi").await;
    let bob_alice_chat = bob.create_chat(&alice).await;

-    tcm.change_addr(&alice, "alice@someotherdomain.xyz").await;
+    tcm.change_addr(&mut alice, "alice@someotherdomain.xyz")
+        .await;

    tcm.section("Bob sends a message to Alice, encrypting to her previous key");
    let sent = bob.send_text(bob_alice_chat.id, "hi back").await;
@@ -63,7 +64,7 @@ async fn check_aeap_transition(chat_for_transition: ChatForTransition) {
    const ALICE_NEW_ADDR: &str = "alice2@example.net";

    let mut tcm = TestContextManager::new();
-    let alice = &tcm.alice().await;
+    let alice = &mut tcm.alice().await;
    let bob = &tcm.bob().await;

    tcm.send_recv_accept(alice, bob, "Hi").await;
@@ -105,10 +106,7 @@ async fn check_aeap_transition(chat_for_transition: ChatForTransition) {
    check_that_transition_worked(bob, &groups, alice_contact, ALICE_NEW_ADDR).await;

    tcm.section("Test switching back");
-    alice
-        .set_primary_self_addr("alice@example.org")
-        .await
-        .unwrap();
+    alice.set_sending_addr("alice@example.org").await;
    let sent = alice
        .send_text(chat_to_send, "Hello from my old addr!")
        .await;
@@ -205,7 +203,7 @@ async fn test_aeap_replay_attack() -> Result<()> {
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn test_write_to_alice_after_aeap() -> Result<()> {
    let mut tcm = TestContextManager::new();
-    let alice = &tcm.alice().await;
+    let alice = &mut tcm.alice().await;
    let bob = &tcm.bob().await;

    let alice_grp_id = chat::create_group(alice, "Group").await?;
@@ -276,14 +276,15 @@ impl ConfiguredLoginParam {
            .await
    }

-    /// Loads legacy configured param. Only used for tests and the migration.
+    /// Loads legacy configured param. Only used for tests and migration 131.
    pub(crate) async fn load_legacy(context: &Context) -> Result<Option<Self>> {
        if !context.get_config_bool(Config::Configured).await? {
            return Ok(None);
        }

        let addr = context
-            .get_config(Config::ConfiguredAddr)
+            .sql
+            .get_raw_config("configured_addr")
            .await?
            .unwrap_or_default()
            .trim()
@@ -480,11 +481,11 @@ pub(crate) async fn save_transport(
    );

    let addr = addr_normalize(&configured.addr);
-    let configured_addr = context.get_config(Config::ConfiguredAddr).await?;
-    let mut modified = context
+    let modified = context
        .sql
-        .execute(
-            "INSERT INTO transports (addr, entered_param, configured_param, add_timestamp)
+        .transaction(|transaction| {
+            let modified = transaction.execute(
+                "INSERT INTO transports (addr, entered_param, configured_param, add_timestamp)
             VALUES (?, ?, ?, ?)
             ON CONFLICT (addr)
             DO UPDATE SET entered_param=excluded.entered_param,
@@ -493,24 +494,18 @@ pub(crate) async fn save_transport(
             WHERE entered_param != excluded.entered_param
                 OR configured_param != excluded.configured_param
                 OR add_timestamp < excluded.add_timestamp",
-            (
-                &addr,
-                serde_json::to_string(entered_param)?,
-                serde_json::to_string(configured)?,
-                add_timestamp,
-            ),
-        )
-        .await?
-        > 0;
+                (
+                    &addr,
+                    serde_json::to_string(entered_param)?,
+                    serde_json::to_string(configured)?,
+                    add_timestamp,
+                ),
+            )? > 0;
+            update_configured_addr(transaction)?;
+            Ok(modified)
+        })
+        .await?;

-    if configured_addr.is_none() {
-        // If there is no transport yet, use the new transport for sending
-        context
-            .sql
-            .set_raw_config(Config::ConfiguredAddr.as_ref(), Some(&addr))
-            .await?;
-        modified = true;
-    }
    Ok(modified)
 }

@@ -625,7 +620,7 @@ pub(crate) async fn sync_transports(
        )
        .collect();

-    let (deleted_ids, reelected) = context
+    let deleted_ids = context
        .sql
        .transaction(|transaction| {
            let mut deleted_ids = Vec::new();
@@ -636,10 +631,10 @@ pub(crate) async fn sync_transports(
                }
                deleted_ids.extend(delete_transport_row(transaction, addr, *timestamp)?);
            }
+            update_configured_addr(transaction)?;
            modified |= !deleted_ids.is_empty();

-            let reelected = maybe_update_sending_transport(transaction)?;
-            Ok((deleted_ids, reelected))
+            Ok(deleted_ids)
        })
        .await?;

@@ -647,12 +642,6 @@ pub(crate) async fn sync_transports(
        purge_transport_caches(context, *transport_id).await;
    }

-    if let Some(new_addr) = reelected {
-        info!(context, "Re-elected sending transport {new_addr:?}.");
-        context.sql.uncache_raw_config("configured_addr").await;
-        modified = true;
-    }
-
    if modified {
        context.self_public_key.lock().await.take();
        context
@@ -711,34 +700,10 @@ pub(crate) async fn purge_transport_caches(context: &Context, transport_id: u32)
    context.metadata.write().await.remove(&transport_id);
 }

-/// Elects another transport for sending if the current one vanished.
-/// Any remaining transport works and selection is anyway moving
-/// to the authority of the SMTP loop, see <https://github.com/chatmail/core/pull/8619>
-pub(crate) fn maybe_update_sending_transport(
-    transaction: &mut rusqlite::Transaction,
-) -> Result<Option<String>> {
-    let configured_addr: String = transaction.query_row(
-        "SELECT value FROM config WHERE keyname='configured_addr'",
-        (),
-        |row| row.get(0),
-    )?;
-    let addrs = transport_addrs(transaction)?;
-    if addrs.contains(&configured_addr) {
-        return Ok(None);
-    }
-    let Some(new_addr) = addrs.into_iter().next() else {
-        return Ok(None);
-    };
-    transaction.execute(
-        "UPDATE config SET value=? WHERE keyname='configured_addr'",
-        (&new_addr,),
-    )?;
-    Ok(Some(new_addr))
-}
-
 /// Adds transport entry to the `transports` table with empty configuration.
 pub async fn add_pseudo_transport(context: &Context, addr: &str) -> Result<()> {
-    context.sql
+    context.sql.transaction(|transaction| {
+        transaction
        .execute(
            "INSERT INTO transports (addr, entered_param, configured_param) VALUES (?, ?, ?)",
            (
@@ -746,8 +711,26 @@ pub async fn add_pseudo_transport(context: &Context, addr: &str) -> Result<()> {
                serde_json::to_string(&EnteredLoginParam{addr: addr.to_string(), ..Default::default()})?,
                format!(r#"{{"addr":"{addr}","imap":[],"imap_user":"","imap_password":"","smtp":[],"smtp_user":"","smtp_password":"","certificate_checks":"Automatic","oauth2":false}}"#)
            ),
+        ).with_context(|| format!("Failed to insert pseudo transport for {addr:?}"))?;
+        update_configured_addr(transaction)?;
+        Ok(())
+    }).await
+}
+
+/// Update deprecated `configured_addr` config so it points to the first transport.
+///
+/// `configured_addr` is not used anymore,
+///  but old core (2026-11) fails when importing a backup without it,
+/// so we need to set it for backwards compatibility.
+pub fn update_configured_addr(transaction: &rusqlite::Transaction) -> Result<()> {
+    transaction
+        .execute(
+            "INSERT OR REPLACE INTO config (keyname, value)
+             SELECT 'configured_addr', addr
+             FROM transports ORDER BY id LIMIT 1",
+            (),
        )
-        .await.with_context(|| format!("Failed to insert pseudo transport for {addr:?}"))?;
+        .context("Failed to update configured_addr")?;
    Ok(())
 }

@@ -197,10 +197,6 @@ async fn test_delete_transport() -> Result<()> {
        .evtracker
        .get_matching(|e| matches!(e, EventType::TransportsModified))
        .await;
-    assert_eq!(
-        alice.get_config(Config::ConfiguredAddr).await?.as_deref(),
-        Some("alice@otherprovider.com")
-    );
    sync_and_check_recipients(alice, alice2, "alice@otherprovider.com").await;

    check_addrs(
@@ -226,50 +222,6 @@ async fn test_delete_transport() -> Result<()> {
    Ok(())
 }

-/// Tests that selecting sending transport by setting "configured_addr" does not
-/// send the sync message, is not synchronized between devices even if sync message is forced,
-/// and does not bump sending transport `add_timestamp`.
-#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
-async fn test_no_configured_addr_synchronization() -> Result<()> {
-    let mut tcm = TestContextManager::new();
-    let alice = &tcm.alice().await;
-    let alice2 = &tcm.alice().await;
-    for a in [alice, alice2] {
-        a.set_config_bool(Config::SyncMsgs, true).await?;
-        a.set_config_bool(Config::BccSelf, true).await?;
-    }
-
-    let addr = "alice@otherprovider.com";
-    add_dummy_transport(alice, addr).await?;
-    send_sync_transports(alice).await?;
-    sync_and_check_recipients(alice, alice2, &format!("{addr} alice@example.org")).await;
-
-    // Selects `addr` on `alice` as the sending transport
-    // and syncs the transport update to `alice2`,
-    // whose own sending transport must stay unchanged.
-    let old_timestamp = add_timestamp(alice2, addr).await;
-    let alice2_primary = alice2.get_config(Config::ConfiguredAddr).await?;
-    alice.set_config(Config::ConfiguredAddr, Some(addr)).await?;
-    assert_eq!(add_timestamp(alice, addr).await, old_timestamp);
-
-    send_sync_transports(alice).await?;
-    alice.send_sync_msg().await?.unwrap();
-    let sync_msg = alice.pop_sent_msg().await;
-    assert_eq!(sync_msg.recipients, format!("alice@example.org {addr}"));
-    // The sync message comes from the new sending address,
-    // which must not make `alice2` adopt it as its own sending address.
-    assert!(sync_msg.payload.contains(&format!("From: <{addr}>")));
-    alice2.recv_msg_trash(&sync_msg).await;
-
-    // add_timestamp must not change.
-    assert_eq!(add_timestamp(alice2, addr).await, old_timestamp);
-    assert_eq!(
-        alice2.get_config(Config::ConfiguredAddr).await?,
-        alice2_primary
-    );
-    Ok(())
-}
-
 /// Tests that `sync_transports()` requests an IO restart
 /// if and only if it modified anything.
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
@@ -288,14 +240,6 @@ async fn test_sync_transports_requests_io_restart() -> Result<()> {
    Ok(())
 }

-async fn add_timestamp(t: &TestContext, addr: &str) -> i64 {
-    t.sql
-        .query_get_value("SELECT add_timestamp FROM transports WHERE addr=?", (addr,))
-        .await
-        .unwrap()
-        .unwrap()
-}
-
 /// Tests that removing the last transport keeps it.
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn test_removing_last_transport() -> Result<()> {
@@ -308,10 +252,6 @@ async fn test_removing_last_transport() -> Result<()> {
    };
    sync_transports(alice, &[], std::slice::from_ref(&removed)).await?;
    assert_eq!(alice.count_transports().await?, 1);
-    assert_eq!(
-        alice.get_config(Config::ConfiguredAddr).await?.as_deref(),
-        Some("alice@otherprovider.com")
-    );

    let removed = RemovedTransportData {
        addr: "alice@otherprovider.com".to_string(),
@@ -319,37 +259,6 @@ async fn test_removing_last_transport() -> Result<()> {
    };
    sync_transports(alice, &[], std::slice::from_ref(&removed)).await?;
    assert_eq!(alice.count_transports().await?, 1);
-    assert_eq!(
-        alice.get_config(Config::ConfiguredAddr).await?.as_deref(),
-        Some("alice@otherprovider.com")
-    );
-    Ok(())
-}
-
-/// Tests which transport is elected for sending.
-#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
-async fn test_maybe_update_sending_transport() -> Result<()> {
-    let t = &TestContext::new_alice().await;
-
-    add_dummy_transport(t, "alice@one.com").await?;
-    assert_eq!(
-        t.sql.transaction(maybe_update_sending_transport).await?,
-        None
-    );
-
-    t.sql
-        .execute(
-            "DELETE FROM transports WHERE addr=?",
-            ("alice@example.org",),
-        )
-        .await?;
-    assert_eq!(
-        t.sql
-            .transaction(maybe_update_sending_transport)
-            .await?
-            .as_deref(),
-        Some("alice@one.com")
-    );
    Ok(())
 }

@@ -0,0 +1,31 @@
+From: Bob <bob@example.net>
+Subject: Message with invalid HTML mime types
+To: alice@example.org
+Message-ID: <html-html-test@localhost>
+Date: Thu, 17 Dec 2020 15:38:45 +0100
+MIME-Version: 1.0
+Content-Type: multipart/mixed;
+ boundary="------------MESSAGE_BOUNDARY"
+Content-Language: en-US
+Chat-Version: 1.0
+
+This is a multi-part message in MIME format.
+--------------MESSAGE_BOUNDARY
+Content-Type: html/plain; charset=utf-8
+Content-Transfer-Encoding: 7bit
+
+This should be ignored.
+
+--------------MESSAGE_BOUNDARY
+Content-Type: html/html; charset=utf-8
+Content-Transfer-Encoding: 7bit
+
+And this should be ignored too.
+
+--------------MESSAGE_BOUNDARY
+Content-Type: text/plain; charset=utf-8
+Content-Transfer-Encoding: 7bit
+
+Here is a text part.
+
+--------------MESSAGE_BOUNDARY--
Author	SHA1	Message	Date
d2weber	eb2e477235	chore: update yerpc 0.7.0 to 0.7.1 (#8868 ) This fixes build problems with the generated jsonrpc qt bindings which occured on UT20.04 builds (uses older qt and gcc versions) It also resolves a cargo future incompatibily warning	2026-10-28 11:59:47 +01:00
link2xt	9e346ac650	refactor!: remove `configured_addr` config configured_addr was already not used by real SMTP code. Rust tests which emulate sending with TestContext.pop_sent_msg() now have a way to set the "sending" address manually in memory.	2026-10-27 11:22:52 +00:00
link2xt	4b8c65e7b4	refactor(smtp): handle closed interrupt channel explicitly Ignoring errors in IMAP code has previously led to busy looping during shutdown in the tests. If interrupt channel is closed, it is better to exit SMTP loop immediately without waiting for the task to be cancelled because if we busy loop the task may even be impossible to cancel.	2026-10-26 16:28:40 +00:00
link2xtandholger krekel	4171c6f74a	chore: update preloaded DNS cache Add all default onboarding relays and remove domains that don't resolve with non-responding IPs. Co-authored-by: holger krekel <holger@merlinux.eu>	2026-10-26 14:05:11 +00:00
holger krekel	5a894d3e37	refactor: read messages inside the markseen_msgs() transaction Ephemeral timers now start in the same transaction instead of a separate one before it.	2026-10-26 15:00:44 +01:00
holger krekel	23b4ca05c8	fix: mark messages seen and queue read receipts in one transaction A failure or an app kill between the separate writes of markseen_msgs() left a message seen without a queued read receipt, read receipt to self or IMAP \Seen flag, and the next check would skip it as already seen.	2026-10-26 15:00:44 +01:00
holger krekel	e11a55c29f	refactor: split a sync insert_imap_markseen() out of markseen_on_imap_table()	2026-10-26 15:00:44 +01:00
holger krekel	5ffcf2a4a4	refactor: make MsgId::start_ephemeral_timer() synchronous A message seen on another device now gets its state and its ephemeral timer in one transaction, so it cannot end up seen without a running timer. A failure to start the timer now fails like a failure to update the state, instead of being only logged.	2026-10-26 15:00:44 +01:00
holger krekel	baec90b70d	refactor: make update_msg_state() synchronous and take a transaction	2026-10-26 15:00:44 +01:00
holger krekel	da3ee2e025	perf: avoid some full table scans on every IMAP loop iteration and sent message On large profiles they keep the CPU busy whenever messages are sent or received.	2026-10-26 14:59:50 +01:00
holger krekel	a4de550a75	refactor: move expiration and IMAP loop queries into constants	2026-10-26 14:59:50 +01:00
link2xt	f3bb558ac3	api!: remove webxdc_realtime_enabled config It is removed from UIs already, so practically not used.	2026-10-26 13:50:35 +00:00
holger krekel	8789098155	chore: add deny.toml exception for RUSTSEC-2026-0387 Timing side channels in crypto-bigint 0.5.5 are fixed only in 0.7.6, but rPGP 0.21 depends on elliptic-curve 0.13 and cx448 0.1, which require crypto-bigint ^0.5. Delta by default uses only Ed25519 and X25519 (and RSA keys from old profiles) that all do not use crypto-bigint.	2026-10-26 12:38:09 +01:00
link2xt	4ad53321f8	chore: upgrade tokio from 1.53.1 to 1.53.3 Makes cargo-deny stop complaining about https://rustsec.org/advisories/RUSTSEC-2026-0386 This is not even a security issue and we don't use mentioned functions anyway.	2026-10-24 17:14:33 +00:00
link2xt	f0be6c387e	fix: ignore html/* MIME parts HTML parts have text/html MIME type. html/* is not a registered MIME type: https://www.iana.org/assignments/media-types	2026-10-24 17:08:12 +00:00
link2xt	4ce056c85c	refactor(scheduler): do not wait for IMAP and SMTP loop to be started If we spawned a task, we alread know that the loop is started, there is no need to send empty value from the task back to the scheduler.	2026-10-24 17:01:05 +00:00
link2xt	df19d9d1df	fix: fix the order of arguments to merge_openpgp_certificates() call This fixes flaky tests/test_securejoin.py::test_qr_scan_updates_new_relay_address which hanged during the second securejoin on fast network (e.g. when testing against local container) as Bob received securejoin pubkey message from Alice but did not merge the new relay list.	2026-10-24 16:52:41 +00:00
link2xt	ca4820aec3	test: add test_import_public_key_tiebreak()	2026-10-24 16:52:41 +00:00
link2xt	a4363aa308	test: add test_merge_openpgp_certificates_tiebreak() This tests that the order of arguments to merge_openpgp_certificates() is important if signature timestamp is the same.	2026-10-24 16:52:41 +00:00
link2xt	6767500ea2	refactor: factor out Contact.relay_addresses()	2026-10-24 16:52:41 +00:00
link2xt	dedc160a2a	refactor: pass current timestamp as an argument to signature_subpackets() pk_encrypt() already uses current timestamp to select the key for encryption, no need to use a potentially different timestamp to sign the message.	2026-10-24 16:52:41 +00:00
link2xt	7a1df15f92	docs: document arguments to secret_key_to_public_key() It is not obvious that relay list is comma-separated.	2026-10-24 16:52:41 +00:00
link2xt	1a632bdade	chore: update clipboard-win from 5.4.0 to 5.4.3 Versions <= 5.4.1 are yanked, apparently because of this change in unsafe code: https://github.com/DoumanAsh/clipboard-win/commit/38c3c3fef175c20ed8f8e33dacb9b1e3bb8eca87 Not a big problem because the crate is only used in repl via rustyline dependency, but cargo-deny complains about the yanked crate. Diff can be viewed at https://cratediff.com/crate/clipboard-win/5.4.0/5.4.3/	2026-10-24 15:28:38 +00:00
link2xt	98289e8dbb	chore: bump verion to 2.66.0-dev	2026-10-22 20:33:10 +00:00
link2xt	706ee7a48c	chore(release): prepare for 2.65.0	2026-10-22 20:19:22 +00:00
link2xt	65da01f863	refactor: create all keyupdates in a single transaction	2026-10-22 20:06:10 +00:00
link2xt	7f3cafd792	refactor: make non_chat_headers() synchronous	2026-10-22 20:06:10 +00:00
link2xt	01fcfc17be	refactor: make insert_into_smtp() synchronous	2026-10-22 20:06:10 +00:00
link2xt	52de603753	refactor: make message::insert_tombstone() synchronous It is only doing SQL, so does not need to be async. This way insert_into_smtp() can use a single transaction to insert a tombstone and enqueue the message.	2026-10-22 20:06:10 +00:00
B. Petersen	4d4ec874d2	chore: remove unused broadcast icon	2026-10-22 21:57:52 +02:00
link2xt	41eed949ac	chore: add deny.toml exception for RUSTSEC-2026-0382 It is a rustls-webpki v0.102.8 dependency of iroh 0.35.0 which cannot be upgraded.	2026-10-22 16:40:22 +00:00
link2xt	53fe350ebb	chore: update webpki-roots 0.26.8 to 0.26.11	2026-10-22 16:40:22 +00:00
link2xt	6bf5c07794	chore: update rustls-webpki 0.103.15 to 0.103.16	2026-10-22 16:40:22 +00:00
biørn	b4cc114195	feat: show info message for unpinning (#8852 ) as recently discussed with @adbenitez and @Amzd, it is better to add an info message also for unpinning a message: otherwise the message "Alice pinned a message" may look like a bug if there is nothing actually pinned as Bob unpinned for whatever reason afterwards. technically, this is a simple change (famous last words) as a messages were always sent on pinning as well as on unpinning, but for unpinning, they were additionally hidden. now the "unpin" info message is visible, however, still tuned down: it is not notified and it does not bubble up in the chatlist (both similar to many info messages about group changes) ftr, this is a minor change, and it should not block ongoing releases wrt pinned messages	2026-10-22 14:55:22 +02:00
link2xt	e16e452091	fix: don't ignore join_next() errors in background_fetch_any() join_next() failing means something went really wrong, e.g. panic inside a task. We also don't cancel the tasks other than by dropping JoinSet, so join_next() should never return an error.	2026-10-22 10:10:09 +00:00
link2xt	26ec01deaa	docs: remove outdated sentence saying QR scan aborts started securejoin processes This is not true since `bbb267331c` and there is a test test_parallel_securejoin()	2026-10-21 04:56:31 +00:00
link2xt	8e9c16baca	chore: update webpki-roots to 1.0.10 It removes compromised emSign CA, see https://emudhra.we-have-a-problem.com/ for details. We have duplicate dependency because of iroh 0.35 still dependencing on the old version, but most important is that IMAP/SMTP connections are using the new version.	2026-10-20 15:44:09 +00:00
link2xt	8d2919d23e	chore: bump version to 2.65.0-dev	2026-10-20 12:02:02 +00:00
link2xt	dd4641071e	chore(release): prepare for 2.64.0	2026-10-20 11:37:33 +00:00
link2xt	7a129352c8	feat: do not copy Chat-Version header into unprotected headers spec.md already documents Header Confidentiality Policy that hides Chat-Version header in encrypted messages, but so far we have copied the header into unprotected headers for compatibility. Since 2.45.0 prefetch does not look at the unprotected Chat-Version do decide if the message should be downloaded (change `b94792706a`) and since 2.50 show_emails setting which controlled whether only "chat messages" are processed is removed (change `63596a4940`).	2026-10-20 10:58:50 +00:00
link2xt	38749e0e9c	fix(imap): do not busy loop if there are no connection candidates and interrupt channel is closed Without connection candidates IMAP busy loops when you try to stop I/O because interrupt channel gets closed and recv() always returns an error immediately, but no connection is attempted afterwards so IMAP loop keeps calling .prepare() in a loop without ever yielding control to executor, so it cannot even be cancelled. New JSON-RPC test test_pseudo_transport_start_stop_io reproduces the problem from CFFI test tests/test_3_offline.py::TestOfflineChat::test_send_lots_of_offline_msgs which added one transport without connection candidates and started I/O.	2026-10-20 10:17:39 +00:00
gluek	c827cb17c8	fix: do not apply channel reaction summaries as reactions A reaction summary of a broadcast channel is sent as an empty reaction to the latest channel message. When another device of the channel owner received it, it removed the owner's own reaction on that message and queued the message for the next summary. So the owner's devices sent the summary to each other, and to all subscribers, every 10 minutes forever.	2026-10-20 08:42:52 +00:00
link2xt	94641df57b	refactor: clean up remaining clippy::arithmetic_side_effects in mimeparser self.parts.remove(i) can panic if "i" is out of range, but now it is obvious that it will not because "i" is returned from position(), and clippy is happy.	2026-10-20 06:45:03 +00:00
link2xt	5de39ba6a4	fix: avoid integer overflow when multiplying received image width by height This is a minor fix, worst case an image with very large dimensions will not be classified as a File. Mostly removing `clippy::arithmetic_side_effects`.	2026-10-20 06:45:03 +00:00
B. Petersen	286c21a1e5	add jsonrpc for get_summary_text	2026-10-19 23:45:55 +02:00
biørn	6dde761ea5	feat: do not spam channel summaries with reactions (#8829 ) while showing reactions for channel summaries was regarded as "let's try" when channel reactions were introduced, meanwhile, after some experience, it only clutters and spams the chatlist. for the subscriber, this is anyways only "you reacted", which is often wrong as there are other reactions. for the owner it is about some names they do not know. the idea of having some "feedback" for the owner is still fulfilled as reactions are (optionally) notified - so owner can still have the "ping ping ping" and relax :) finallly, this is also what telegram is doing with their channels	2026-10-19 20:30:30 +02:00
link2xt	9637ecff6b	ci: test with Python 3.15 Also moved python version to environment variable so status checks will be named "JSON-RPC Python tests (ubuntu-latest, latest)" instead of "JSON-RPC Python tests (ubuntu-latest, 3.14)" and we don't have to update the list of required status checks each time the version changes. We already do the same for Rust.	2026-10-18 13:04:38 +00:00
WofWca	dce6438d95	refactor: move `call_state_ext` to `CallInfo`	2026-10-16 14:49:42 +00:00
WofWca	151f12b724	fix: races in `get_summary_text_ext`, improve perf Remove the two unnecessary DB calls that fetch the message (which could possibly be different from the current `Message`). Now the only async thing in `get_summary_text_ext` that remains is `get_webxdc_info`. See https://github.com/chatmail/core/pull/8826.	2026-10-16 14:49:42 +00:00
pancake	d62438d03c	fix: abort scheduler tasks after shutdown timeout (#8832 ) The timeout currently owns each IMAP and SMTP JoinHandle. When 30 seconds elapse, dropping the timeout drops the handle and detaches the task instead of cancelling it. On Haiku, a network task stuck behind a missed or delayed socket wakeup can therefore outlive scheduler shutdown, retaining connections and interfering with restart or active-account deletion. Borrow each handle while waiting, then explicitly abort and await it if shutdown times out. This guarantees that scheduler shutdown does not complete while a timed-out network task is still running.	2026-10-16 10:14:29 +00:00
link2xt	60e1d59182	chore: bump rustls from 0.23.45 to 0.23.46 This fixes https://rustsec.org/advisories/RUSTSEC-2026-0346 https://rustsec.org/advisories/RUSTSEC-2026-0347 https://rustsec.org/advisories/RUSTSEC-2026-0348 https://rustsec.org/advisories/RUSTSEC-2026-0349	2026-10-16 08:33:45 +00:00
Hocuri	64e58755c0	fix: Encode '@' with '%40' again in QR codes (#8825 ) Fix #8824 This commit fixes the following problem: This is a Delta Chat invite link: https://i.delta.chat/#CFAE4957FFEB8529CC1A5CF568D0EFE4139D5749&v=3&x=8lJEkOodZ01W-Xz5sOvAI1JN&i=XonKX2YYHM14I5c-PBj3YAED&s=Pc4aW8eePr_lO1OFnwUJ5fVB&a=pbkwwo8z7%40nine.testrun.org&r=uydmygf8t@chat.vim.wtf,13xe893jx%40tarpit.fun&n=Alice&g=Great+group It's linkified correctly on Github, but WhatsApp makes only part of the link clickable, so that the inviter name gets lost. A group invite link additionally loses the group name and gets converted into a 1:1 invite. When I replace the `@` with `%40`, it gets linkified correctly. Apparently, WhatsApp tries to be smart and assumes that if there is an `@` in the link, it's almost over, and treats any non-ascii character as the end of the link. ...So, if we want our links to render correctly on WhatsApp, I guess we do need to replace `@` with `%40`. That's a very simple one-line fix (plus tests). It will just make the links look a little bit uglier.	2026-10-14 17:18:30 +02:00
link2xt	d766641ce2	feat: switch to another SMTP transport when current one returns an error Classic email servers sometimes start rejecting all messages and ask the user to solve web CAPTCHA, but still allow to connect. In this case we want to switch to another SMTP server by moving the transport to the end of the list returned by smtp::sorted_transports. We disconnect after any message sending failure, so next message or resent same message will be sent over another other transport. Permanent SMTP error does not necessarily mean that switching to another server will help. For example if the user tries to send a large message, any server will reject it, and it is not a failure of the server. We do not try to distinguish between error messages, so it is expected that we may sometimes switch to another server when it is unnecessary.	2026-10-13 00:43:51 +00:00
link2xt	5510fb5a18	refactor(smtp): introduce smtp::Connection structure It is now impossible for SMTP client to be connected without having a From address and transport_id available. Follow-up to `70730490b2`	2026-10-12 23:35:58 +00:00
link2xt	036b928a7f	feat: take key flags and expiration into account when selecting the key Test keys were generated with GnuPG 2.4.9 from Arch Linux. The script that was used to generate the key for test_select_pk_for_encryption: ``` export GNUPGHOME="$PWD/gnupghome" rm -fr "$GNUPGHOME" mkdir -p "$GNUPGHOME" chmod 700 "$GNUPGHOME" # --faked-system-time example is from the gpg man page GPG="gpg --batch --quiet --faked-system-time 20070924T154812" USERID='Alice <alice@example.org>' # Generate the primary key. # "default" means certification+signing primary key # "never" to make the key not expire, otherwise gpg generates expiring key by default. $GPG --passphrase '' --quick-generate-key "$USERID" ed25519 default never # --quick-add-key requires that keys are referred to by the fingerprint. # Output of --with-colons is described in /usr/share/doc/gnupg/DETAILS FINGERPRINT="$($GPG --list-secret-keys --with-colons \| awk -F: '$1 == "fpr" { print $10 }')" # Authentication-only RSA key, should not be used for encryption. $GPG --passphrase '' --quick-add-key "$FINGERPRINT" rsa auth never # Expired (considering the fake date) subkey. $GPG --passphrase '' --quick-add-key "$FINGERPRINT" cv25519 encr 1d # Signing subkey. $GPG --passphrase '' --quick-add-key "$FINGERPRINT" ed25519 sign never # Usable encryption subkey. $GPG --passphrase '' --quick-add-key "$FINGERPRINT" cv25519 encr never # Expiring subkey that is not expired in the beginning of 2008. $GPG --passphrase '' --quick-add-key "$FINGERPRINT" cv25519 encr 1y # Another encryption subkey that should not be used because the first one is preferred. $GPG --passphrase '' --quick-add-key "$FINGERPRINT" cv25519 encr never $GPG --armor --export "$FINGERPRINT" > alice.tpk.asc ``` Key for test_select_only_expired_subkey was generated with: ``` #!/bin/sh set -e export GNUPGHOME="$PWD/gnupghome" rm -fr "$GNUPGHOME" mkdir -p "$GNUPGHOME" chmod 700 "$GNUPGHOME" GPG="gpg --batch --quiet --faked-system-time 20070924T154812" USERID='Alice <alice@example.org>' $GPG --passphrase '' --quick-generate-key "$USERID" ed25519 default never FINGERPRINT="$($GPG --list-secret-keys --with-colons \| awk -F: '$1 == "fpr" { print $10 }')" $GPG --passphrase '' --quick-add-key "$FINGERPRINT" cv25519 encr 1y $GPG --armor --export "$FINGERPRINT" > alice.tpk.asc ``` Key for test_expiring_subkey_selection was generated with: ``` #!/bin/sh set -e export GNUPGHOME="$PWD/gnupghome" rm -fr "$GNUPGHOME" mkdir -p "$GNUPGHOME" chmod 700 "$GNUPGHOME" GPG="gpg --batch --quiet" USERID='Alice <alice@example.org>' $GPG --passphrase '' --faked-system-time 20250101T000000 --quick-generate-key "$USERID" ed25519 default never FINGERPRINT="$($GPG --list-secret-keys --with-colons \| awk -F: '$1 == "fpr" { print $10 }')" $GPG --passphrase '' --faked-system-time 20250101T000000 --quick-add-key "$FINGERPRINT" cv25519 encr never $GPG --passphrase '' --faked-system-time 20260601T000000 --quick-add-key "$FINGERPRINT" cv25519 encr 1m $GPG --passphrase '' --faked-system-time 20260601T000000 --quick-add-key "$FINGERPRINT" cv25519 encr 2w $GPG --passphrase '' --faked-system-time 20260608T000000 --quick-add-key "$FINGERPRINT" cv25519 encr 2w $GPG --armor --export "$FINGERPRINT" > alice.tpk.asc ```	2026-10-10 21:01:24 +00:00
link2xt	f3b043f111	refactor: remove Context argument from secret_key_to_public_key()	2026-10-10 21:01:24 +00:00
link2xt	694ef8ba76	chore: bump version to 2.64.0-dev	2026-10-09 17:59:58 +00:00
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