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
    2022-10-02T11:54:20+00:00

    I have exactly the same problem.

    Mail attachments are displayed even under „sent“ mails but don’t arrive at the recipients mailbox.

    macOS Montery v12.5 with Apple M1 Max, 32GB

    Microsoft Outlook for Mac v16.65 (22091101) (no update available)

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  2. Anonymous
    2022-09-14T17:55:11+00:00

    One thing I have noticed is that when I experience the issue is that Outlook for Mac is showing the size of the attachment at 0 KB. If I click on the attachment before it disappears, I can see the file correctly.

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  3. Anonymous
    2022-09-14T16:34:16+00:00

    Nice catch. Without SMIME no problem.

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  4. Anonymous
    2022-09-14T00:26:41+00:00

    Hello Nathan,

    Can you please open a support ticket, you can do this from the Outlook Help Menu > Contact Support. We want to collect specific information about this issue to help investigate.

    Thanks,

    Pawan

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  5. Anonymous
    2022-09-14T00:16:00+00:00

    This issue just started for me on September 12, 2022.

    Mac OS Monterey 12.4

    MacBook Pro 2021, Apple M1 Max

    Outlook 16.65

    Office 365 higher education account

    Has happened with various file types including PDF, XLS, DOC, JPG.

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