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

Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.

0 comments

240 answers

Sort by: Newest
Most helpful Newest Oldest
  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.

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  2. Anonymous
    2023-08-21T09:30:46+00:00

    Did anyone already file a support ticket for this at Hubspot? Maybe it's their fault and they need to update the Plugin?

    Great job on finding the root cause everyone! :)

    Was this answer helpful?

    0 comments
  3. Anonymous
    2023-08-18T20:21:09+00:00

    I must say that my issues began with installing the Hubspot plugin and stopped after reverting to the old one, removing the Hubspot plugin and updating to the new version again. Now it is working again for 3 weeks, flawless.

    Was this answer helpful?

    2 people found this answer helpful.
    0 comments
  4. Anonymous
    2023-08-18T15:15:53+00:00

    I got a notification today to update my desktop Outlook. After updating to 16.76 and restarting, I was able to send attachments with no additional actions.

    Was this answer helpful?

    0 comments
  5. 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.

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments