"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
    2024-04-11T22:50:40+00:00

    Agree - Glad i started this post as so many people are affected by this!

    I've troubleshooted this to death and there is no pattern.

    For us, certain email addresses are affected for a few days at a time and then moves on to someone else in the business.

    I wish Apple would create their own decent mail and office system so we can all tell **** to do one and go away!

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  2. Anonymous
    2024-04-11T14:03:42+00:00

    100%, not the prob. No third-party plugins and certainly no Jira.

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  3. Anonymous
    2024-04-11T13:31:58+00:00

    We are not using Jira. My impression was that it relates to the length of the email. Shorter email replies are more likely to get stuck.

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  4. Anonymous
    2024-04-11T13:20:43+00:00

    Hi guys,

    I might have found the trigger for this issue.

    Are you guys using Jira?

    We downgraded jira to not include some integrations with microsoft and i feel that i have been issue-free for 2 days now. It might actually be this.

    Like 6 months ago, Microsoft told me to remove all third party plugins in Outlook in an effort to solve the issue and it did not work, but now when we have removed some stuff in Jira i feel a difference.

    Can it be that easy?

    (I'm running Outlook 16.84 on Mac OS Sonoma 14.4.1 Mac Studio 2022 Apple M1 Max)

    I'll let you know if i encounter this issue again.

    Sincerely,

    A hopeful production manager

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  5. Anonymous
    2024-04-08T16:13:40+00:00

    Happened to me again this week. Not once, but TWICE on the same email, and therefore my clients didn't get a status update until Sunday because #OutlookNotSoGood failed to send again. This long-term bug is making your users look stupid, @microsoft. Address this.

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