"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
    2024-03-21T09:26:58+00:00

    I've had this issue for almost a year now...

    I have also been in contact with Microsoft about it and nothing has worked..

    I can't believe this issue is still ongoing, but what to expect, Microsoft is a small indie developer with a low number of staff, we have to respect that it will take a few years more.

    No but seriously, solve this issue!

    One note to add, I have 2 accounts in my client, one iCloud and one Microsoft, and the iCloud is not having these issues, it is only related to Microsoft account if that helps the trouble shooting.

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  2. Anonymous
    2024-03-20T23:56:33+00:00

    I am having exactly the same issue.

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  3. Anonymous
    2024-03-20T13:33:50+00:00

    Same issue for me - many messages are getting stuck in drafts unable to send, despite other outbound emails sending fine at the same time.

    Haven't been able to narrow down the cause, but once it decides it doesn't want to allow a reply in a particular thread, it wont ever allow it within the desktop app.

    The only workaround which has worked out of all the above for me is to allow the message to enter Drafts, then head to mobile, find it in drafts and send from there. Seems to work.

    Not a workable long term solution.

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  4. 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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  5. 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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