diff --git a/src/scheduler.rs b/src/scheduler.rs
index f32fb41c2..b41bb0d0e 100644
--- a/src/scheduler.rs
+++ b/src/scheduler.rs
@@ -1,3 +1,4 @@
+use std::cmp;
 use std::iter::{self, once};
 use std::num::NonZeroUsize;
 use std::sync::atomic::Ordering;
@@ -6,6 +7,7 @@ use anyhow::{bail, Context as _, Error, Result};
 use async_channel::{self as channel, Receiver, Sender};
 use futures::future::try_join_all;
 use futures_lite::FutureExt;
+use rand::Rng;
 use tokio::sync::{oneshot, RwLock, RwLockWriteGuard};
 use tokio::task;
 
@@ -707,8 +709,9 @@ async fn smtp_loop(
         loop {
             if let Err(err) = send_smtp_messages(&ctx, &mut connection).await {
                 warn!(ctx, "send_smtp_messages failed: {:#}", err);
-                timeout = Some(timeout.map_or(30, |timeout: u64| timeout.saturating_mul(3)))
+                timeout = Some(timeout.unwrap_or(30));
             } else {
+                timeout = None;
                 let duration_until_can_send = ctx.ratelimit.read().await.until_can_send();
                 if !duration_until_can_send.is_zero() {
                     info!(
@@ -716,14 +719,9 @@ async fn smtp_loop(
                         "smtp got rate limited, waiting for {} until can send again",
                         duration_to_str(duration_until_can_send)
                     );
-                    tokio::time::timeout(duration_until_can_send, async {
-                        idle_interrupt_receiver.recv().await.unwrap_or_default()
-                    })
-                    .await
-                    .unwrap_or_default();
+                    tokio::time::sleep(duration_until_can_send).await;
                     continue;
                 }
-                timeout = None;
             }
 
             // Fake Idle
@@ -737,17 +735,23 @@ async fn smtp_loop(
             // sending is retried (at the latest) after the timeout. If sending fails
             // again, we increase the timeout exponentially, in order not to do lots of
             // unnecessary retries.
-            if let Some(timeout) = timeout {
+            if let Some(t) = timeout {
+                let now = tokio::time::Instant::now();
                 info!(
                     ctx,
-                    "smtp has messages to retry, planning to retry {} seconds later", timeout
+                    "smtp has messages to retry, planning to retry {} seconds later", t,
                 );
-                let duration = std::time::Duration::from_secs(timeout);
+                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();
+                let slept = (tokio::time::Instant::now() - now).as_secs();
+                timeout = Some(cmp::max(
+                    t,
+                    slept.saturating_add(rand::thread_rng().gen_range((slept / 2)..=slept)),
+                ));
             } else {
                 info!(ctx, "smtp has no messages to retry, waiting for interrupt");
                 idle_interrupt_receiver.recv().await.unwrap_or_default();