diff --git a/src/com/fsck/k9/controller/MessagingController.java b/src/com/fsck/k9/controller/MessagingController.java
index 2ebbc847f..8b96d2946 100644
--- a/src/com/fsck/k9/controller/MessagingController.java
+++ b/src/com/fsck/k9/controller/MessagingController.java
@@ -3045,6 +3045,15 @@ public class MessagingController implements Runnable {
                         }
 
                     } catch (Exception e) {
+                        // 5.x.x errors from the SMTP server are "PERMFAIL"
+                        // move the message over to drafts rather than leaving it in the outbox
+                        // This is a complete hack, but is worlds better than the previous
+                        // "don't even bother" functionality
+                        if (getRootCauseMessage(e).startsWith("5")) {
+                            localFolder.moveMessages(new Message[] { message }, (LocalFolder) localStore.getFolder(account.getDraftsFolderName()));
+                        } else {
+                        }
+
                         message.setFlag(Flag.X_SEND_FAILED, true);
                         Log.e(K9.LOG_TAG, "Failed to send message", e);
                         for (MessagingListener l : getListeners()) {
@@ -3064,7 +3073,11 @@ public class MessagingController implements Runnable {
                 l.sendPendingMessagesCompleted(account);
             }
             if (lastFailure != null) {
-                notifySendFailed(account, lastFailure);
+                if (getRootCauseMessage(lastFailure).startsWith("5")) {
+                    notifySendPermFailed(account, lastFailure);
+                } else {
+                    notifySendTempFailed(account, lastFailure);
+                }
             }
         } catch (UnavailableStorageException e) {
             Log.i(K9.LOG_TAG, "Failed to send pending messages because storage is not available - trying again later.");