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
    2022-10-14T14:50:29+00:00

    as far as I could test, and from what I see on the other posts, it is only for SMIME (signed/encrypted) emails.

    If you do not use one of the 2 you should be fine. Or at least this is what the behavior indicates so far.

    right now I am on 16.66 and so far it looks good. I have only send about 10 emails but at least so far all of them had the attachments.

    My understanding is (from several people here in the office that do not have S/MIME etc. enabled) the problem still exists when receiving emails encoded with SMIME/encrypted etc, because then it remains active and replying or forwarding them affects those attached files.

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  2. Anonymous
    2022-10-14T07:12:08+00:00

    I was using 16.65 and had the problem without using signed/encrypted emails.

    I removed the entire office suite and am using 16.62 now which doesn't appear to have the problem. I will not move back to the most recent version until I get confirmation that the problem (which is already lasting for 3 months!) has been resolved by Microsoft.

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  3. Anonymous
    2022-10-14T06:15:48+00:00

    as far as I could test, and from what I see on the other posts, it is only for SMIME (signed/encrypted) emails.

    If you do not use one of the 2 you should be fine. Or at least this is what the behavior indicates so far.

    right now I am on 16.66 and so far it looks good. I have only send about 10 emails but at least so far all of them had the attachments.

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  4. Anonymous
    2022-10-14T01:44:50+00:00

    This is specific to users sending emails with digitally signed or encrypted emails. Is it relevant to those of us who do NOT send digitally signed or encrypted emails through Outlook?

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  5. Anonymous
    2022-10-13T18:27:58+00:00

    News Flash!

    According to Microsoft this is fixed with version 16.66, see:

    https://support.microsoft.com/en-us/topic/outlook-fails-to-send-attachments-and-inline-images-when-sending-a-signed-or-encrypted-email-using-the-new-outlook-for-mac-5719ab3c-70cd-4e19-8025-e51b7e055efa

    Wait! I know that several people here still report the issue with 16.66 and 16.67 (on the beta channel).

    Any comments from anyone who has tested this further? We had two people who had not switched to "Legacy" Outlook that one worked, the other didn't.

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