"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

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  1. Anonymous
    2023-10-06T20:35:16+00:00

    I've got a new issue in the past few days. When I reply to a message it show a small notification saying "creating draft" then the new message immediately is moved to drafts rather then open a new compose window. Happens about 50% of the time. The signatures and images are still being stripped. I tried removing all plugins (only had Hubspot) but didn't help

    I still can't believe that 2+ weeks later this issue hasn't been resolved and seems to be getting worse.

    What is anyone else on this ticket current status?

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  2. Anonymous
    2023-10-09T13:59:33+00:00

    I also have this same issue. About every 1/10 emails does not send and appears with the "Message failed to send" red error box.

    Hopefully Microsoft fix this soon because it is very frustrating.

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  3. Anonymous
    2023-10-23T14:23:32+00:00

    Same issue here, only solve is to open OWA and send from there.

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  4. Anonymous
    2023-11-03T01:23:04+00:00

    Same issue here (O365, New Outlook, Mac running Sonoma 14.0)

    I tested a workaround (thanks, reddit) and it worked:

    When you get the 'fail to send' error message, use Command + S to Save the message, then send. I just tried it and it worked for me. Fingers crossed it will keep working, and hopefully this will give the MS engineers something to guide them on where the problem is.

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  5. Anonymous
    2023-11-06T17:35:54+00:00

    No such luck for me.

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