"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
    2024-05-01T21:44:29+00:00

    Same issue here. On a Mac. Only temporary fix is once I get that error I just go to Outlook Web. It saves in my drafts instantly so I just go to my Drafts and hit send from the web and continue on with my life.

    What's annoying though, is if you send it from the Web, the email doesn't show up in your sent on the Mac Outlook App...only if you look in your Sent folder on the Web.

    Super frustrating...

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  2. Anonymous
    2024-04-29T17:56:55+00:00

    Same issue here. Cant get it to stop.

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  3. Anonymous
    2024-04-22T13:00:57+00:00

    Getting this constantly today on Version 16.84 (24041420) and Mac OS 14.4.1 (23E224).

    Seems to work after closing and reopening outlook

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  4. Anonymous
    2024-04-22T07:25:01+00:00

    Has this been fixed yet?!?

    It is a year later and I am still having issues with emails not being sent and finding them in Drafts days later.

    Come on Microsoft - is it too much to expect that Outlook can reliably send emails !!!!!

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  5. Anonymous
    2024-04-17T13:31:09+00:00

    We currently have two users with this issue, very recently, since 16.83.2 update.

    Waiting for this to slowly happen on our very important client who all use macs....

    Hoping it is patched before then but

    Legacy version of Outlook works just fine - it's very clearly a problem with the "new" app rather than anything else.

    It does also seem to be replies in particular, probably with embedded images in them, haven't got that far yet!

    I suppose I will have to raise a support request for this and spend about a month trying to communicate with support...

    Please. Fix. This

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