diff --git a/src/pretix/api/webhooks.py b/src/pretix/api/webhooks.py
index d5113d7ddc..ee553b11ca 100644
--- a/src/pretix/api/webhooks.py
+++ b/src/pretix/api/webhooks.py
@@ -250,7 +250,7 @@ def send_webhook(self, logentry_id: int, action_type: str, webhook_id: int):
                     webhook.enabled = False
                     webhook.save()
                 elif resp.status_code > 299:
-                    raise self.retry(countdown=2 ** (self.request.retries * 2))
+                    raise self.retry(countdown=2 ** (self.request.retries * 2))  # max is 2 ** (8*2) = 65536 seconds = ~18 hours
             except RequestException as e:
                 WebHookCall.objects.create(
                     webhook=webhook,
@@ -262,6 +262,6 @@ def send_webhook(self, logentry_id: int, action_type: str, webhook_id: int):
                     payload=json.dumps(payload),
                     response_body=str(e)[:1024 * 1024]
                 )
-                raise self.retry(countdown=2 ** (self.request.retries * 2))
+                raise self.retry(countdown=2 ** (self.request.retries * 2))  # max is 2 ** (8*2) = 65536 seconds = ~18 hours
         except MaxRetriesExceededError:
             pass
diff --git a/src/pretix/base/services/mail.py b/src/pretix/base/services/mail.py
index 8d9c90fb23..d547bb7afc 100644
--- a/src/pretix/base/services/mail.py
+++ b/src/pretix/base/services/mail.py
@@ -372,7 +372,7 @@ def mail_send_task(self, *args, to: List[str], subject: str, body: str, html: st
             backend.send_messages([email])
         except smtplib.SMTPResponseException as e:
             if e.smtp_code in (101, 111, 421, 422, 431, 442, 447, 452):
-                self.retry(max_retries=5, countdown=2 ** (self.request.retries * 2))
+                self.retry(max_retries=5, countdown=2 ** (self.request.retries * 3))  # max is 2 ** (4*3) = 4096 seconds = 68 minutes
             logger.exception('Error sending email')
 
             if order:
@@ -389,7 +389,7 @@ def mail_send_task(self, *args, to: List[str], subject: str, body: str, html: st
             raise SendMailException('Failed to send an email to {}.'.format(to))
         except Exception as e:
             if isinstance(e, (smtplib.SMTPServerDisconnected, smtplib.SMTPConnectError, ssl.SSLError, OSError)):
-                self.retry(max_retries=5, countdown=2 ** (self.request.retries * 2))
+                self.retry(max_retries=5, countdown=2 ** (self.request.retries * 3))  # max is 2 ** (4*3) = 4096 seconds = 68 minutes
             if order:
                 order.log_action(
                     'pretix.event.order.email.error',