"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
    2024-07-23T07:50:07+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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  2. 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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  3. 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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  4. Anonymous
    2024-07-18T12:44:38+00:00

    Just started to happen to me yesterday on 7-17-24. I do recall an update running just before then. I am going to change my update settings from "Current Channel" to Beta and see if that helps resolve.

    I was previously using:

    • Current Channel is 16.87 (New Outlook for Mac)

    Just updated to:

    • Beta Channel is 16.88 (New Outlook for Mac)

    Tested the same email that failed in version 16.87. Now in version 16.88 the email did go through, but it still sat in my Outgoing folder for about 5-7 seconds and then finally sent. Makes me think something is still jacked up.

    I actually restarted my Mac yesterday and that seemed to help for a while too. Going to do that again for today.

    Thanks

    Patrick

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  5. Anonymous
    2024-07-12T09:50:33+00:00

    I have the same issue every now and then.

    May I add to this ticket that a error message without any information whatsoever is not really good UI design. I was pestering our internal team with mail sending errors for quite some time before they where able to confirm that the problem lies with the client, not the server. This could have been analyzed a lot faster and easier if there where at least some usable log available providing information about what went wrong within Outlook.

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