Outlook 365 for Mac - not sending attachments

Anonymous

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?

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240 answers

Anonymous

2022-10-04T05:37:20+00:00

Yes indeed , it is a "known issue". We cannot see the history of the bug, which would be great to actually see when it was filled. The only thing we know for sure is that they started investigating 2 weeks ago.

The most problematic part on the story is that people noticed this and reported on the beta versions as it seems and they still went on and released it with that bug included.
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Anonymous

2022-10-03T17:13:44+00:00

I am here to echo the frustration and confusion. The software that I pay hundreds of dollars a year for is broken in a fundamental way. Microsoft, please escalate this issue!
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Anonymous

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

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

The above link shows that it is a know issue and still MS is working it. Not sure how many decades will pass before they resolve
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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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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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