diff --git a/postman/src/sender.rs b/postman/src/sender.rs
index eaffab9..66a01f9 100644
--- a/postman/src/sender.rs
+++ b/postman/src/sender.rs
@@ -361,8 +361,9 @@ WHERE
             let now = Utc::now();
             let mut updated_reminder_time =
                 self.utc_time.with_timezone(&self.timezone.parse().unwrap_or(Tz::UTC));
+            let mut fail_count = 0;
 
-            while updated_reminder_time < now {
+            while updated_reminder_time < now && fail_count < 4 {
                 if let Some(interval) = self.interval_months {
                     if interval != 0 {
                         updated_reminder_time = updated_reminder_time
@@ -372,6 +373,7 @@ WHERE
                                     "{}: Could not add {} months to a reminder",
                                     interval, self.id
                                 );
+                                fail_count += 1;
 
                                 updated_reminder_time
                             });
@@ -380,13 +382,14 @@ WHERE
 
                 if let Some(interval) = self.interval_days {
                     if interval != 0 {
-                        if let Some(new_time) =
-                            updated_reminder_time.checked_add_days(Days::new(interval as u64))
-                        {
-                            updated_reminder_time = new_time
-                        } else {
-                            warn!("{}: Could not add {} days to a reminder", self.id, interval);
-                        }
+                        updated_reminder_time = updated_reminder_time
+                            .checked_add_days(Days::new(interval as u64))
+                            .unwrap_or_else(|| {
+                                warn!("{}: Could not add {} days to a reminder", self.id, interval);
+                                fail_count += 1;
+
+                                updated_reminder_time
+                            })
                     }
                 }
 
@@ -395,7 +398,11 @@ WHERE
                 }
             }
 
-            if self.expires.map_or(false, |expires| updated_reminder_time > expires) {
+            if fail_count >= 4 {
+                error!("Reminder {} failed to update 4 times and so is being deleted", self.id);
+
+                self.force_delete(pool).await;
+            } else if self.expires.map_or(false, |expires| updated_reminder_time > expires) {
                 self.force_delete(pool).await;
             } else {
                 sqlx::query!(