diff --git a/authentik/stages/email/tasks.py b/authentik/stages/email/tasks.py
index db9c72d34..59ebf6e63 100644
--- a/authentik/stages/email/tasks.py
+++ b/authentik/stages/email/tasks.py
@@ -91,7 +91,7 @@ def send_mail(
                 messages=["Successfully sent Mail."],
             )
         )
-    except (SMTPException, ConnectionError) as exc:
+    except (SMTPException, ConnectionError, OSError) as exc:
         LOGGER.debug("Error sending email, retrying...", exc=exc)
         self.set_status(TaskResult(TaskResultStatus.ERROR).with_error(exc))
         raise exc