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
    2023-08-08T19:37:56+00:00

    I have the same issue! Hope the 8/16/23 update works as well. Thanks for sharing.

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  2. Anonymous
    2023-08-04T14:11:18+00:00

    This is happening more and more. This thread was started in May 2022. And so far, Microsoft has not determined the issue, and it is getting very frustrating. There are at least 18 pages of people trying to get someone to figure out the issue.

    Is this issue being worked on?

    What is the eta for the fix?

    Many have been paying for this service for a very long time, and it hasn't been reliable for over a year! We need communication from Microsoft!

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  3. Anonymous
    2023-08-02T15:41:31+00:00

    One other thing I did was change the default for viewing PDFs via the Finder to the Apple Preview App vs Adobe which I believe someone else had mentioned earlier in the thread. Between this and making sure the extended experiences was checked has worked for over a week now using MS Outlook for Mac v 16.75.2. Hope the issue goes away for everyone soon as I understand the frustration.

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  4. Anonymous
    2023-08-01T08:29:27+00:00

    No-one in my team has the Hubspot plugin installed, so this is either compounding the problem or co-incidence I suspect.

    There must be something underlying this that is causing the issue.

    For now, upgrading to 16.76 (BETA) has solved the issue for everyone in my organisation.

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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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