"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
    2023-10-05T05:27:32+00:00

    Another update - problems started again yesterday, for me its definitely when an email has embedded images and i'm replying or forwarding. After spending an hour or so in chat to Microsoft support, this time a dedicated team who look after Outlook for Macs, they finally admitted that they have received other calls relating to this and had been escalated to a senior tech to investigate and would probably be fixed in future updates!!!

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  2. Anonymous
    2023-09-28T06:36:08+00:00

    Possible fix!!

    Removed my auto signature from Replies and Forwarding, been working fine since then

    Have been in contact with Microsoft support who appear to have no interest in solving this.

    Get the usual rubbish - "What version of Mac, What version of Outlook" Blah blah blah!!

    Would be cool but didn't work for me. I don't have a response signature at all. Hope it works out for you though!

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  3. Anonymous
    2023-09-28T03:52:48+00:00

    Possible fix!!

    Removed my auto signature from Replies and Forwarding, been working fine since then

    Have been in contact with Microsoft support who appear to have no interest in solving this.

    Get the usual rubbish - "What version of Mac, What version of Outlook" Blah blah blah!!

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  4. Anonymous
    2023-09-25T15:07:16+00:00

    same here.

    Outlook Version 16.77

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  5. Anonymous
    2023-09-21T11:14:08+00:00

    Nothing changed on my side. If anything, then it got worse today. Could send one out of 20, maybe.

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