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
    2022-09-15T05:55:08+00:00

    I raised a support ticket and got a reply today. At least the issue is now on the bug list.

    Outlook fails to send attachments and inline images when sending a signed or encrypted email using the new Outlook for Mac

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  2. Anonymous
    2022-09-29T09:42:19+00:00

    Its 29 September 2022 and I am still experiencing this issue. I cannot work like this...

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  3. 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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  4. Anonymous
    2022-10-03T06:23:46+00:00

    For some reason we are having more and more incoming complains for this in the past month.

    I cannot understand how an issue like this is still not fixed after almost 5 months

    This renders Outlook useless for Business usage ( I guess for home as well for those that use SMIME)

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  5. Anonymous
    2022-10-03T06:30:59+00:00

    Oh yeah, I forgot to mention that I use S/MIME but didn't had a problem with that. Looks like the error appeared for me a few weeks ago when the first recipients complain about non-existent attachments.

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