From 78caa6f53c8efdb116c589132fcf42797d6422ba Mon Sep 17 00:00:00 2001
From: link2xt <link2xt@testrun.org>
Date: Wed, 16 Sep 2026 20:22:20 +0000
Subject: [PATCH] fix: emit SmtpMessageSent event after deleting the message
 from SMTP queue

This is mostly needed to fix flaky
tests/test_something.py::test_is_sending_finished
by making sure that is_sending_finished() return false
once we got an event that message was sent.
---
 src/smtp.rs      | 17 +++++++++++++----
 src/smtp/send.rs |  9 ---------
 2 files changed, 13 insertions(+), 13 deletions(-)

diff --git a/src/smtp.rs b/src/smtp.rs
index 4de52f144..56ca6ca44 100644
--- a/src/smtp.rs
+++ b/src/smtp.rs
@@ -467,16 +467,16 @@ pub(crate) async fn send_msg_to_smtp(
         let split_index = usize::try_from(chunk_size.min(unsent_len))
             .context("Failed to convert SMTP chunk size")?;
         let (chunk, rest) = unsent.split_at(split_index);
-        let status = smtp_send(context, chunk, body.as_str(), smtp, Some(msg_id)).await;
-        if !matches!(status, SendResult::Success) || rest.is_empty() {
-            break status;
-        }
         for sent_to_addr in chunk {
             let sent_to_addr_string = sent_to_addr.to_string();
             if !sent_to_set.insert(sent_to_addr_string) {
                 error!(context, "Attempted to send to {sent_to_addr} twice.");
             }
         }
+        let status = smtp_send(context, chunk, body.as_str(), smtp, Some(msg_id)).await;
+        if !matches!(status, SendResult::Success) || rest.is_empty() {
+            break status;
+        }
         let sent_to_str = sent_to_set
             .iter()
             .map(|a| a.as_ref())
@@ -499,6 +499,15 @@ pub(crate) async fn send_msg_to_smtp(
                 .sql
                 .execute("DELETE FROM smtp2 WHERE id=?", (rowid,))
                 .await?;
+
+            let sent_to_len = sent_to_set.len();
+            debug_assert!(sent_to_len > 0);
+            let info_msg = format!(
+                "Message len={} was SMTP-sent to {sent_to_len} recipients.",
+                body.len()
+            );
+            info!(context, "{info_msg}.");
+            context.emit_event(EventType::SmtpMessageSent(info_msg));
         }
         SendResult::Failure(ref err) => {
             if err
diff --git a/src/smtp/send.rs b/src/smtp/send.rs
index d48920c4f..bcdd103b0 100644
--- a/src/smtp/send.rs
+++ b/src/smtp/send.rs
@@ -5,7 +5,6 @@ use async_smtp::{EmailAddress, Envelope, SendableEmail};
 use super::Smtp;
 use crate::config::Config;
 use crate::context::Context;
-use crate::events::EventType;
 use crate::log::warn;
 use crate::tools;
 
@@ -39,8 +38,6 @@ impl Smtp {
             context.ratelimit.write().await.send();
         }
 
-        let message_len_bytes = message.len();
-
         let envelope =
             Envelope::new(self.from.clone(), recipients.to_vec()).map_err(Error::Envelope)?;
         let mail = SendableEmail::new(envelope, message);
@@ -55,12 +52,6 @@ impl Smtp {
 
         transport.send(mail).await.map_err(Error::SmtpSend)?;
 
-        let info_msg = format!(
-            "Message len={message_len_bytes} was SMTP-sent to {} recipients.",
-            recipients.len()
-        );
-        info!(context, "{info_msg}.");
-        context.emit_event(EventType::SmtpMessageSent(info_msg));
         self.last_success = Some(tools::Time::now());
         Ok(())
     }