"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
    2024-07-24T07:12:26+00:00

    I am going to give this a shot - Probably the most useful answer I've seen. Great work! This has been so frustrating

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  2. Anonymous
    2024-07-23T19:21:17+00:00

    this prolem appeared 2-3 days ago for me as well

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  3. Anonymous
    2024-07-23T07:50:07+00:00

    Hello,

    I"m on 16.87 Current Channel for Mac, issue started after a reboot yesterday. Downgraded to Legacy version this morning - seems to fix the issue.

    Cheers,

    Gerald

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  4. Anonymous
    2024-07-23T07:23:26+00:00

    Hey everyone,

    Just chiming in here since I've been running into the exact same issue! I initially thought it might be a problem with a specific email account or server, but then I realized it's mainly happening with my Microsoft Exchange accounts in Outlook. Interestingly enough, my Gmail account in Outlook is working just fine.

    After some digging around, I stumbled upon a solution that seems to work pretty well.

    In Outlook, go to Settings > Composing > Wait to send messages for, and increase that interval. I started with 5 seconds, and it definitely helped, but didn't completely eliminate the "Message sending failed" errors. Bumping it up to 10 seconds has almost fixed the issue for me – I still get the error occasionally, but it's super rare now. I'm using Microsoft Outlook 16.87 on macOS Sonoma 14.5, by the way.

    Hopefully, this little trick does the trick for you guys too! Let me know if it makes a difference on your end.

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  5. Anonymous
    2024-07-22T08:54:59+00:00

    I have the same issue.

    I probably get the error with 1 in 10 emails; the dreaded noise (blunk) and the red box. I just keep trying to resend and it usually eventually sends without error. It is just a bit annoying. Please fix it!.

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