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
    2023-07-31T14:56:35+00:00

    Mine is on and still having the issues. :-(

    We are also connected to HubSpot. Wonder how many here are?

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  2. Anonymous
    2023-07-31T08:53:45+00:00

    Does anyone know if Microsoft is actively working to resolve this?

    I've tried a number of the suggestions and work arounds in this thread but unfortunately none of them have been successful!

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  3. Anonymous
    2023-07-31T07:13:58+00:00

    This could indeed be the solution.

    Now you mention it, I encountered this issue also after installing the Hubspot plugin.

    I changed from the new version to the old version and then 2 days later back to the new version. I don't have any issue anymore with sending attachments so far, this setting (you mention below) is "on", I don't know if it was on when I had the issues.

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  4. 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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  5. Anonymous
    2023-07-25T10:38:18+00:00

    My fix was to revert to the legacy version but as of today it's forcing me onto the new one.

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