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

Anonymous

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

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155 answers

Anonymous

2023-12-26T13:31:05+00:00

Solution

Help--> Revert to legacy UI
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Anonymous

2023-12-26T14:09:03+00:00

I'm experiencing the same issue.

It only occurs when I choose a sensitivity tag that is restricted for my company.
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Anonymous

2024-01-03T20:35:25+00:00

I had the same. Tried restarting the app, rebooting the Mac, restarting the router, nada.

Eventually I just copied the text I'd written, discarded the draft, popped up a fresh reply, pasted the text in, and sent. Went without issues.
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Anonymous

2024-01-04T18:55:45+00:00

I have started to have this same experience as of 1/2. The only remedy that I have found is to open another email window and then copy/paste the same information, then send it from there. That seems to work each time.
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Anonymous

2024-01-10T16:15:29+00:00

I have the exact same issue. This REEKS Microsoft! The team should be ashamed.

No fix on my end legacy or otherwise.
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