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
    2022-10-03T13:18:16+00:00

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  2. Anonymous
    2022-10-03T12:05:32+00:00

    I also believe that this is probably not a MacOS issue since as you mentioned this happens on several versions of the OS, but it seems to have broken only to the newest versions of Outlook.

    I also believe that it also affects inline signatures with images, since these are also considered attachments. I have tested this as well on multiple accounts on different Macs and they all behave the same.

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  3. Anonymous
    2022-10-03T07:48:47+00:00

    Me and my workmate, both working with MacOS Outlook, have the same problem.

    we both use s/mime and since a while can't send attachments anymore if we sign the mails with s/mime.

    it is possible to send signed mails without attachments.

    it is also possible to send attachments if the mail is unsigned.

    if I switch back from "new outlook" to the "old" outlook, everything works fine, means i can send signed mails with attachments.

    I'm experiencing this problem on three different: Macs, BigSur, catalina, mojave, thus i don't think it's related to macOS version rather an recent outlook update.

    currently running: 16.65 (22091101)

    I also tested with the newest beta but experience the same issue.

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  4. 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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  5. 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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