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
    2023-08-21T22:24:01+00:00

    I don't use Hubspot and I still have the attachment issue, so I don't think Hubspot is the root cause, sadly.

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  2. Anonymous
    2023-08-24T17:04:58+00:00

    Same as everyone -

    Mine is PDF attachments disappear.

    I can then reply all to the send message missing the attachment and re-attach and it then works.

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  3. Anonymous
    2023-08-24T20:33:23+00:00

    Hi Benjamin, I updated Outlook 365 to the last version 16.76 and the problem seems gone. We also use HubSpot and I already asked our IT to open a support ticket to check the issue on their side.

    I have 16.76 and the issue still persists.

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  4. Anonymous
    2023-08-24T21:23:06+00:00

    We removed the HubSpot add-in from all devices and everyone is able to send attachments without issue.

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  5. Anonymous
    2023-08-25T03:03:19+00:00

    Hi All,

    we recently upgraded to the new version,

    Sending mail attachments would remove when sending to emails.

    Steps involved to try and fix that didn't work:

    1. Uninstalling all Microsoft Outlook files and reinstalling. (didn't work)
    1. Removing Microsoft license. (didn't work)

    None of these options worked.

    What worked

    The only fix for us was to downgrade just office. we selected V16.59 but maybe a slightly newer version will work until Microsoft fix these issues.

    Follow the Uninstall all Microsoft Outlook files procedure. then install via the Update history for Office file supplied bellow.

    Link here for anyone with the issues.

    Update history for Office for Mac - Office release notes | Microsoft Learn

    Hope this helps while Microsoft get their act together :)

    PS. don't forget to turn off mac office auto updates.

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