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
    2023-08-18T14:26:26+00:00

    Just to add my 2cents. I've had this issue for a few months now, and like many others I use the HubSpot plugin and need it enabled.

    Based on the recommendation of others, I reverted Outlook back to Legacy (under the Help Menu). This has been the best workaround and allows me to send attachments and continue to use the HubSpot Plugin.

    When the new version came out a week ago, I installed, changed back to "New Outlook" and enabled the plugin. Almost instantly, I couldn't send attachments. Again, I went back to Legacy mode and everything is working again.

    I hope this helps.

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  2. Anonymous
    2023-08-18T14:22:53+00:00

    Hi All

    We have certainly found success in removing the Hubspot plugin. However, we can't operate without using it.

    So what has worked for our affected users, was to switch back the legacy Outlook client. This has resolved all issues for us. Though it's not aesthetically pleasing, it's functional.

    Thanks

    Matt

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  3. Anonymous
    2023-08-18T14:17:09+00:00

    Someone posted a work around of working off line to send the email (click outlook, then work offline) after the email has sent, go back to work online. I don’t want to remove hubspot and this has worked every time for me. Just ridiculous that I have to remember to do this every time I send an email with attachments. What are Microsoft playing at with the fix

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  4. Anonymous
    2023-08-18T14:07:00+00:00

    Hi Alex, I'm curious to know if the removal Hubspot is still working for you re: missing attachments. I just saw this discussion thread. I'm having the same issue and it just started a week or 2 ago. Super big problem for anyone running a business.

    Is that fix still working for you? Any other insights that might help.

    Thx!
    Dan

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  5. Anonymous
    2023-08-18T12:49:46+00:00

    It's been 4 days since I removed the HubSpot Add-On and so far, all the attachments are sending.

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