Outlook 365 for Mac - not sending attachments

Anonymous
2022-05-27T14:24:12+00:00

I have an issue whereby Outlook for Mac is losing attachments when sending emails (typically, but not exclusively, PDF files).

If a file(s) is/are dragged and dropped into an email it is shown as attached and appears to send as normal. There are no error messages or bouncebacks, and the first we know that the email has lost the attachment is when we are advised by the recipient. Then when checking the sent folder, the email is there but again without the attachments.

Doesn't do this every-time though... sometimes the email goes with the attachments as it normally should.

I'm using version 16.62 (22052500)

Has anybody else had this issue and is there a fix? Or is it a software glitch?

Outlook | MacOS | Legacy Outlook for Mac | For home

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  1. Anonymous
    2022-10-10T22:36:40+00:00

    What version did you upgrade to?

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  2. Anonymous
    2022-10-10T22:04:33+00:00

    I updated to the latest version of Outlook today and I'm able to once again send signed emails with the attachments being included for the recipient.

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  3. Anonymous
    2022-10-09T23:17:28+00:00

    After searching for the answer and getting frustrated, I did the oldest trick in the book. Turned the computer off and back on. Voila everthing is attaching now. I am using Mac OS Monetary 12.5.1

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  4. Anonymous
    2022-10-07T21:08:51+00:00

    Seeing this issue as well. M1, Intel-based mac

    Mail attachments are displayed even under the sent folder but don’t arrive at the recipient's mailbox

    We use S/MIME. Turning it off seems to help for a while. but eventually comes back.

    Microsoft Outlook for mac 16.66.(22100201) and older version

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  5. Anonymous
    2022-10-05T17:02:13+00:00

    I experience exactly the same behavior.

    Outlook 365 For Business on Mac OS (Macbook Pro / M1 / S-MIME certificate configured).

    Attachments are silently ignored.

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