"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
    2024-03-14T05:16:47+00:00

    Having the same issue, Version 16.83.

    This is more than a nuisance: the fact that such a basic function on a critical app is not working, apparently for many many months now, is an indicator that something is very wrong inside the Microsoft organization.

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  2. Anonymous
    2024-03-13T19:05:59+00:00

    I just experienced this issue AGAIN. Can't believe this still hasn't been resolved all these months later. Outlook for Mac is trash. I don't want to have to delete embedded images from an email thread just for my emails to be sent. Does anyone have any other solutions to this?

    Couple of workarounds:

    1. Let the email enter drafts on Mac. Use outlook on mobile to send draft. The email just goes very easily.
    2. Switch accounts once or twice (incase of multiple accounts on same outlook) and then send. Again email gets sent easily).

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  3. Anonymous
    2024-03-13T17:57:25+00:00

    I just experienced this issue AGAIN. Can't believe this still hasn't been resolved all these months later. Outlook for Mac is trash. I don't want to have to delete embedded images from an email thread just for my emails to be sent. Does anyone have any other solutions to this?

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  4. Anonymous
    2024-03-04T12:42:16+00:00

    I have the same issue and this is what is working fir me:

    I have multiple email accounts in Outlook. If I select a different "from" account and then switch it back to the one I used initially, the message is sent successfully.

    Multiple users with this same issue here and this workaround worked.

    very odd.

    I will recommend legacy view until this issue is fixed!

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  5. Anonymous
    2024-02-28T21:11:26+00:00

    I have the same issue and this is what is working fir me:

    I have multiple email accounts in Outlook. If I select a different "from" account and then switch it back to the one I used initially, the message is sent successfully.

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