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
    2023-08-21T09:51:49+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.

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  2. Anonymous
    2023-08-18T14:57:34+00:00

    All, I was hesitant to update in case something went wrong, again, but here is what I've found through my testing over the past month or so.

    I was running the Legacy version with the Hubspot plugin and didn't have nay issues. I no longer use Hubspot so, after seeing other post about removing this I revert back to the NEW version and removed the Hubspot plugin. Since then I've had no issues....touch wood!!!

    I believe that anyone using Hubspot should revert to the Legacy version, and anyone NOT using Hubspot should remove the plug in if they want to use the NEW version.

    Only my opinion and what I've seen personally over the past few weeks.

    However, the sentiment still remains as to why we need to do these types of testing and troubleshooting for such a large corporation is beyond me.

    Hope this helps anyone struggling with this issue til Microsoft resolve it.

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  3. 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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  4. Anonymous
    2023-08-17T19:46:06+00:00

    Removing the Hubspot add in from my Microsoft Outlook for Mac Version 16.75.1. has so far today fixed the issue.

    Again one day only, but a huge improvement since my attachments would only make it in my emails 50% of the times.

    Thank you for the suggestions in this chat.

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  5. Anonymous
    2023-08-17T16:12:03+00:00

    This recent update seems to have had no positive impact. Regrettably, we find ourselves back at square one with the initial problems remaining unresolved. Throughout the morning, I've experienced repeated issues with my emails, specifically with missing attachments. A tech giant like Microsoft must ensure that such foundational functions operate seamlessly. Immediate attention to this matter would be highly appreciated, but do not hold your breath, because these guys MOVE SLOW and I've lost confidence in their ability to find a solution.

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