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
    2023-08-08T13:02:20+00:00

    I am encountering this issue as well -- it has occurred sporadically over the last 60 days or so. I have tried everything to address the problem (restart computer, close/re-open Outlook, etc.) and cannot count the number of responses I receive saying "There was nothing attached to your email."

    Even when/if I forward an email containing an attachment, the attachment is often dropped (i.e. attachment not included on the email to the recipient).

    I now have to send any email w/ an attachment via the outlook.office.com web portal. Extrememly frustrating. Hoping the 8/16/23 update fixes this issue.

    **2021 14" MacBook Pro M1

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  2. NoOneCan 7,805 Reputation points Volunteer Moderator
    2023-08-04T14:20:52+00:00

    There is a recent incident EX637339.

    Title: Some users' email with attachments sent from Outlook for Mac may be delivered without attachments

    User impact: Users' email with attachments sent from Outlook for Mac may be delivered without attachments.

    More info: Users can verify if they’ve encountered this problem in Outlook for Mac by reviewing their Sent Items to validate if a sent message contains an attachment. If users don't see the attachment, they can reply to the message in their Sent Items folder to reattach and send the message again. Current status: We're continuing to develop an Outlook for Mac update that will correct this issue, that we still expect it will be available for download in mid-August. We anticipate providing a release date by our next communication update.

    Scope of impact: This issue is specific to a very small percentage of users' email with attachments sent from Outlook for Mac.

    Start time: Tuesday, July 11, 2023 at 4:08 AM GMT+8

    Root cause: A conflict occurring with how our service detects attachment IDs before sending email in Outlook for Mac is resulting in the service removing attachments on sending email.

    Next update by: Wednesday, August 16, 2023 at 2:30 AM GMT+

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  3. 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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  4. 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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  5. 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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