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
    2023-08-08T13:02:20+00:00

    I am encountering this issue as well -- it has occurred sporadically over the last 60 days or so. I have tried everything to address the problem (restart computer, close/re-open Outlook, etc.) and cannot count the number of responses I receive saying "There was nothing attached to your email."

    Even when/if I forward an email containing an attachment, the attachment is often dropped (i.e. attachment not included on the email to the recipient).

    I now have to send any email w/ an attachment via the outlook.office.com web portal. Extrememly frustrating. Hoping the 8/16/23 update fixes this issue.

    **2021 14" MacBook Pro M1

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  2. Anonymous
    2023-07-28T16:40:55+00:00

    Hi all, I may have found something that could help (someone may have already mentioned this) as I was made aware that some plugins may be causing my pdf sending issue. When I went in to remove one of the plugins (Hubspot) I noticed that in my Outlook for Mac app in the Privacy Settings the "Turn on optional connected experiences" (see image) which seems to underpin the Plugin functionality, mine was turned off somehow. When I turned it back on and restarted the app, I was able to send an email with attached pdfs which did not work previously. Have not tested a ton, but seems to be working. Good luck everyone as this has been one of the most frustrating issues I have come across in years...

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  3. Anonymous
    2023-07-14T13:13:03+00:00

    I have the same issue but I noticed that also images are not being sent. And I also discovered that I only have the issue when a mailinggroup is the receiver (TO or CC). So when I am sending to a mailinggroup with several email addresses, I have the issue.

    Mac office version: 16.76

    Mac OS 13.4.1

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  4. Anonymous
    2023-07-14T12:39:53+00:00

    Hi, I just started having this issue about 3 weeks ago. Same as described. Any updates on fixes?

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  5. Anonymous
    2023-07-12T15:18:00+00:00

    I have tried to revert Outlook to Legacy and it worked.

    I've reverted to legacy across our team and some people are still being affected unfortunately.

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