feat: do not use ConfiguredAddr when connecting to SMTP

src/config.rs

@@ -42,10 +42,12 @@ use crate::{constants, stats};
 #[strum(serialize_all = "snake_case")]
 pub enum Config {
     /// Deprecated(2026-04).
-    /// Use ConfiguredAddr, [`crate::login_param::EnteredLoginParam`],
-    /// or add_transport{from_qr}()/list_transports() instead.
     ///
-    /// Email address, used in the `From:` field.
+    /// Email address used by the deprecated configure() procedure.
+    ///
+    /// Use add_transport{from_qr}() to configure new transports,
+    /// Use list_transports() to learn about configured transports,
+    /// including their addresses.
     Addr,
 
     /// Deprecated(2026-04).
@@ -195,9 +197,9 @@ pub enum Config {
     #[strum(props(default = "0"))]
     DeleteDeviceAfter,
 
-    /// The address of the transport used for sending.
+    /// Deprecated(2026-09).
     ///
-    /// Device-local, other devices choose their own sending transport.
+    /// Use ConfiguredLoginParam and list_transports() instead.
     ConfiguredAddr,
 
     /// Deprecated(2026-04).

src/ephemeral/ephemeral_tests.rs

@@ -684,6 +684,10 @@ async fn test_ephemeral_msg_offline() -> Result<()> {
     check_msg_will_be_deleted(alice, msg.id, &chat, now, now + i64::from(duration) + 1).await?;
     assert!(alice.sql.exists(stmt, (msg.id,)).await?);
 
+    alice
+        .assert_warn("No SMTP connection candidates provided")
+        .await;
+
     Ok(())
 }
 

src/message/message_tests.rs

@@ -631,6 +631,10 @@ async fn test_delete_msgs_offline() -> Result<()> {
     delete_msgs(alice, &[msg.id]).await?;
     assert!(!alice.sql.exists(stmt, (msg.id,)).await?);
 
+    alice
+        .assert_warn("No SMTP connection candidates provided")
+        .await;
+
     Ok(())
 }
 

src/smtp.rs

@@ -98,19 +98,36 @@ impl Smtp {
         }
 
         self.connectivity.set_connecting(context);
-        let (_transport_id, lp) = ConfiguredLoginParam::load(context)
-            .await?
-            .context("Not configured")?;
         let proxy_config = ProxyConfig::load(context).await?;
-        self.connect(
-            context,
-            &lp.smtp,
-            &lp.smtp_password,
-            &proxy_config,
-            &lp.addr,
-            lp.strict_tls(proxy_config.is_some())?,
-        )
-        .await
+        let transports = ConfiguredLoginParam::load_all(context).await?;
+
+        // Try to connect to the newest transport first. If sending is unreliable,
+        // user can configure a new transport and it will be the one used.
+        // Conversely, if user just added a new transport and sending got less reliable,
+        // user can restore old state by removing the just added transport.
+        for (transport_id, lp) in transports.into_iter().rev() {
+            info!(context, "Trying to connect to transport {transport_id}.");
+            match self
+                .connect(
+                    context,
+                    &lp.smtp,
+                    &lp.smtp_password,
+                    &proxy_config,
+                    &lp.addr,
+                    lp.strict_tls(proxy_config.is_some())?,
+                )
+                .await
+            {
+                Ok(()) => return Ok(()),
+                Err(err) => {
+                    warn!(
+                        context,
+                        "Failed to connect to SMTP transport {transport_id}: {err:#}."
+                    );
+                }
+            }
+        }
+        bail!("Failed to connect to any SMTP server");
     }
 
     /// Connect using the provided login params.