"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
    2024-06-14T09:26:09+00:00

    Hello,

    When you say updated everything is that the latest Mac OS as well as Outlook?

    I will give this a try on one of the machines that is having the problem to see if it rectifies the problem.

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  2. Anonymous
    2024-06-13T23:07:59+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

    We have not had any issues for over a month now. I'm sure I'm going to jinx it by sending this. We have everything updated to current versions
    Version 16.86 for Outlook. Before this we were getting issues every day

    Hopefully the last update solved this - fingers crossed

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  3. Anonymous
    2024-06-13T15:31:35+00:00

    We have a customer who has also had this happen to their Outlook on their Macs. Again an intermittent issue but they have updated again today to say the problem is still happening.

    Do we know if Microsoft are aware of this issue properly or do I need to log a call with their hopeless support?

    I've not tried any workarounds as of yet as I'm unsure of what to try.

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  4. Anonymous
    2024-06-12T16:07:11+00:00

    I'm baffled why Microsoft hasn't addressed this issue. Because they think it's only affecting a "small group of users"? - they need to realize that only a very small percentage of people will complain or comment on a thread like this. It took me months of having this problem to finally search deeper and discover this thread and learn that I'm "not alone".

    A year seems like plenty of time to resolve this "bug". Work-arounds are not an acceptable answer anymore.

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  5. Anonymous
    2024-06-03T13:40:30+00:00

    I tried a few different ideas from various responses. Deleting embedded images didn't work. Deleting everything in the thread, including my signature, worked. But then I tried to just copy my reply and paste to a new reply and that also worked. So it seems totally random what works and what doesn't. Really frustrating in any case and another reason I dislike "New" Outlook (kind of like "New Coke" years ago). Also hate that I can't delete attachments when people send me huge files I don't need to save.

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