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
    2023-07-31T16:20:10+00:00

    I also have Outlook connected to HubSpot (also use the plugin).

    However, the problem has disappeared since I started using the latest Bata version of Outlook.

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  2. Anonymous
    2023-07-31T16:36:12+00:00

    Unfortunately, I don't have the option of using the Beta version yet. No updates and I have my beta option turned on. So not sure why I haven't gotten the option to try the Beta version yet.

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  3. Anonymous
    2023-07-31T16:45:27+00:00

    Check this out. Have you already done it this way?:

    https://insider.microsoft365.com/en-us/join/Mac

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  4. Anonymous
    2023-07-31T16:53:55+00:00

    Yes, already tried that. Says mine is updated already, but it isn't the Beta version that others are getting. I have automatically update and Beta Channel chosen but still not in the Beta version. No clue why.

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  5. Anonymous
    2023-08-01T07:56:30+00:00

    Thanks Jim

    I was suffering from this issue (no attachments or inline images), which was resolved by upgrading to the 16.76 beta. However, it today started happening again.

    "Turn on optional connected experiences" was checked. However, I found turning it off (restarting app) then turning it on (restarting app) fixed the issue again - at least for now.

    I too have the Hubspot plugin installed, so wondering whether there is a weird interaction going on here.

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