"Message failed to send" Red Error box in Outlook 365 for Mac

Anonymous
2023-08-14T06:11:51+00:00

Hi everyone - has anyone had issues with sending emails using Outlook 365 for Macs? Especially a red error box that appears at the bottom (attached) and says "Message failed to send Open" The email is then stuck in drafts with the option to continue editing but it is simply frozen in drafts and the only way is to delete and try again. Alternatively, you can go to the webmail version of outlook, find the drafts folder and send from there. This has been happening on/off for several weeks now, no pattern, just happens occasionally.

This version of Outlook 365 is absolutely **** with so many issues

Outlook | MacOS | Legacy Outlook for Mac | For home

Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.

0 comments No comments

155 answers

Sort by: Oldest
  1. Anonymous
    2024-07-03T01:44:12+00:00

    I'm still having this issue, and I'm updated to the latest versions of Mac and Outlook.

    I have to delete attachments in-line from signatures from other people's emails in a thread to work. Very frustrating.

    Was this answer helpful?

    0 comments No comments
  2. Anonymous
    2024-07-03T02:35:55+00:00

    This is back. After a long time...this error is back.

    Was this answer helpful?

    0 comments No comments
  3. Anonymous
    2024-07-03T12:18:20+00:00

    This seems to be happening more and more for me, I'm on Outlook 16.88, but I have found a workaround that so far has worked every time. When this error comes up, I quit Outlook, re-launch, then click in the Inbox the email thread, and then on the Draft message in the thread I click 'Resume Editing' button on the right, then Send.

    Was this answer helpful?

    0 comments No comments
  4. Anonymous
    2024-07-04T05:54:38+00:00

    Multiple people in my organisation are having the same issue.

    I suggest everyone who is having this same issue open a support ticket, Microsoft does not appear to be listening to this thread.

    Was this answer helpful?

    0 comments No comments
  5. Anonymous
    2024-07-04T06:22:29+00:00

    Multiple people in my organisation are having the same issue.

    I suggest everyone who is having this same issue open a support ticket, Microsoft does not appear to be listening to this thread.

    That's when I found this thread. When support told me to raise it here and wouldn't raise an escalated but ticket or similar. :-/

    Was this answer helpful?

    0 comments No comments