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"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
    2024-12-03T17:27:47+00:00

    I fixed it. I went back to the Legacy version, and had no further issues. Hey Microsoft! I'm not your unpaid beta tester! Get your poop in group before you foist a product on us.

    1 person found this answer helpful.
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  2. Anonymous
    2024-12-01T05:46:39+00:00

    Spent an hour trying to reinstall the app with no luck. Reverted back to legacy version everything works fine immediately.

    From the top bar: Help> Revert to Legacy Version

    Microsoft- Get your act together

    Apple- Fix Mac Mail. Its absolute garbage.

    1 person found this answer helpful.
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  3. 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.

    1 person found this answer helpful.
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  4. Anonymous
    2023-09-14T10:49:26+00:00

    I have exactly the same issue, as do multiple of my colleagues.

    • We all use New Outlook (currently version 16.77)
    • OS is updated to newest version (Ventura 13.5.2)
    • I've tried from multiple profiles

    I've tried attaching picture, but it just says "File(s) failed to upload", so I uploaded the screenshot here: https://snipboard.io/Mk5VpO.jpg

    Is there anywhere a log can be fetched?

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  5. Anonymous
    2023-08-14T08:49:00+00:00

    Hi David,

    Thank you for visiting Microsoft Community, we are glad to be of your assist.

    As per your description shared, we understand you are encounterring email sending issue in Outlook for Mac, however, we do not see your screenshot thus, to provide possible solution, kindly collect below information for us, thanks in advance:

    Hope above is helpful and we looking forward your update, thank you for your time.

    Regards,

    Microsoft Community

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