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Using Outlook 2019 and Windows 10. Tried to send an email with with a 14 MByte attachment. Mail was not sent and shows up in Outbox Folder.

Outlook then set to Work Offline. Attempts to delete email included:

  • Highlight email and press Delete button
  • Right click on email and select delete.
  • Highlight email and select delete icon from Outlook menu
  • Right click folder and select Delete All. In this case, I receive a confirmation dialogue, but the mail does not get deleted.
  • Right click on email and select Move/Drafts. Mail does not get moved.
  • Attempt to open mail and remove attachment. Result shown below.

Error message when attempting to open email

I also restarted not only Outlook, but Windows, and tried all that again with the same results. I also tried running Outlook in Safe Mode, but no joy.

Finally, I tried the web interface provided by my ISP, but that does not show an Outbox folder.

Is there anything else I can try?

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After trying a variety of things, I succeeded as follows.

  • Switch from Working Offline to Connected
  • Initiate Send/Receive (F9 key)
  • Cancel the send task from the Send/Receive dialogue.
  • Highlight the email and delete it with the Delete key.

I don't know how or why this method succeeded, I know only that it did.

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You may need to try creating a new temporary default pst file:

  1. Create a new pst-file: Ribbon tab: Home-> button: New Items-> More Items-> Outlook Data File
  2. Set this pst-file as the default data file in your Account Settings: File-> Account Settings-> Account Settings-> tab Data Files
  3. When you now restart Outlook, your original pst-file will show up as the secondary set of mailbox folders. From here, you should be able to move the message from the Outbox folder or even delete the entire Outbox folder (when you do, make sure you also delete it from the Deleted Items folder or hold the SHIFT button when deleting the folder to bypass the Deleted Items folder).
  4. Set the original pst-file as the default delivery location again via the same method as above and restart Outlook. If you deleted the Outbox folder, it will automatically be recreated and will be empty
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  • Thank you for this answer. Regrettably, when I got to Step 3, I got the same results as before. It was worth a shot though. – Dan Bracuk Jan 9 '20 at 18:08

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