diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2c0e286ad..d9ebd5ecb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -17,6 +17,7 @@
 - speed up loading of chat messages #3171
 - clear more columns when message expires due to `delete_device_after` setting #3181
 - do not try to use stale SMTP connections #3180
+- retry message sending automatically if loop is not interrupted #3183
 
 ### Changes
 - add more SMTP logging #3093
diff --git a/src/scheduler.rs b/src/scheduler.rs
index fd4f044d2..e1e88c288 100644
--- a/src/scheduler.rs
+++ b/src/scheduler.rs
@@ -305,6 +305,7 @@ async fn smtp_loop(ctx: Context, started: Sender<()>, smtp_handlers: SmtpConnect
             .expect("smtp loop, missing started receiver");
         let ctx = ctx1;
 
+        let mut timeout = None;
         let mut interrupt_info = Default::default();
         loop {
             let job = match job::load_next(&ctx, Thread::Smtp, &interrupt_info).await {
@@ -322,9 +323,16 @@ async fn smtp_loop(ctx: Context, started: Sender<()>, smtp_handlers: SmtpConnect
                     interrupt_info = Default::default();
                 }
                 None => {
-                    if let Err(err) = send_smtp_messages(&ctx, &mut connection).await {
+                    let res = send_smtp_messages(&ctx, &mut connection).await;
+                    if let Err(err) = &res {
                         warn!(ctx, "send_smtp_messages failed: {:#}", err);
                     }
+                    let success = res.unwrap_or_default();
+                    timeout = if success {
+                        None
+                    } else {
+                        Some(timeout.map_or(30, |timeout: u64| timeout.saturating_mul(3)))
+                    };
 
                     // Fake Idle
                     info!(ctx, "smtp fake idle - started");
@@ -333,7 +341,23 @@ async fn smtp_loop(ctx: Context, started: Sender<()>, smtp_handlers: SmtpConnect
                         Some(err) => connection.connectivity.set_err(&ctx, err).await,
                     }
 
-                    interrupt_info = idle_interrupt_receiver.recv().await.unwrap_or_default();
+                    if let Some(timeout) = timeout {
+                        info!(
+                            ctx,
+                            "smtp has messages to retry, planning to retry {} seconds later",
+                            timeout
+                        );
+                        let duration = std::time::Duration::from_secs(timeout);
+                        interrupt_info = async_std::future::timeout(duration, async {
+                            idle_interrupt_receiver.recv().await.unwrap_or_default()
+                        })
+                        .await
+                        .unwrap_or_default();
+                    } else {
+                        info!(ctx, "smtp has no messages to retry, waiting for interrupt");
+                        interrupt_info = idle_interrupt_receiver.recv().await.unwrap_or_default();
+                    };
+
                     info!(ctx, "smtp fake idle - interrupted")
                 }
             }
diff --git a/src/smtp.rs b/src/smtp.rs
index a1c1bfb15..b1bbeb679 100644
--- a/src/smtp.rs
+++ b/src/smtp.rs
@@ -483,10 +483,9 @@ pub(crate) async fn send_msg_to_smtp(
 ///
 /// Logs and ignores SMTP errors to ensure that a single SMTP message constantly failing to be sent
 /// does not block other messages in the queue from being sent.
-pub(crate) async fn send_smtp_messages(
-    context: &Context,
-    connection: &mut Smtp,
-) -> anyhow::Result<()> {
+///
+/// Returns true if all messages were sent successfully, false otherwise.
+pub(crate) async fn send_smtp_messages(context: &Context, connection: &mut Smtp) -> Result<bool> {
     context.send_sync_msg().await?; // Add sync message to the end of the queue if needed.
     let rowids = context
         .sql
@@ -504,10 +503,12 @@ pub(crate) async fn send_smtp_messages(
             },
         )
         .await?;
+    let mut success = true;
     for rowid in rowids {
         if let Err(err) = send_msg_to_smtp(context, connection, rowid).await {
             info!(context, "Failed to send message over SMTP: {:#}.", err);
+            success = false;
         }
     }
-    Ok(())
+    Ok(success)
 }