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
    2022-09-12T08:54:57+00:00

    This issue also happens with Office 365 on a corporate account... I work for an university and all employees and students work with Office 365 (or MS 365 as it seems to be called now?). I recently returned from holiday so I can't tell for sure when or with what Outlook version this issue with losing attachments started to occur. I'm currently working with Outlook version 16.64 (22082100) which I installed via the Mac App Store. It was updated about 2 weeks ago. My Mac runs Monterey 12.5.1. On all occasions I can see the mail including the attachment in my sent items folder in Outlook or the web interface. But a lot of recipients complain the attachment is not included when they receive my mail. These are mostly colleagues that are part of the same organization in Office 365.

    So it doesn't only occur with Google mail services, also with Microsofts very own Office 365 this problem occurs.

    After reading here that switching back to the old layout of Outlook seems to fix this issue, I also switched back. I held back this switch for quite a while since a few basic features such as S/MIME signing (and encrypting) mail with the new Outlook wasn't possible for a long, long time. I've been a Office user for a long time and have seen various versions of Outlook for Mac throughout the years, but something as basic as attachments getting dropped along the way is a new all time low for me...

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  2. Anonymous
    2022-09-12T10:22:12+00:00

    Having the same problem on Outlook 365 16.65 (the latest available on "Current Channel (Preview)", latest MacOS.

    Either dragging attachments in from other emails, or attaching them manually from files located witihn the filesystem shows them being attached, and also shows the attachments in the Sent folder, but the recipient doesn't receive them.

    Switching to the "old Outlook" fixes it.

    How can such basic functionality end up broken, and missed on deployment?

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  3. Anonymous
    2022-09-12T19:10:42+00:00

    Hello Nathan,

    Sorry to hear about the issue you are experiencing. This needs a detailed investigation. Can you please reach out to support, we need additional information to troubleshoot this issue. You can contact support by hitting the Outlook Help Menu > Contact Support.

    Thanks,

    Pawan Kapoor

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  4. Anonymous
    2022-09-12T19:33:15+00:00

    First... Be aware to whom you are responding to... I'm not Nathan

    And this is simply frustrating that there are a lot of threads escalating the issue for the last few months but you people are just still investigating the issue. Are you people using a different mail client for interactions which sends the attachments without any issues? If yes, please let me know so that i can switch over to that rather than just using Ms365 since i don't want to waste my money on some crappy application and unhelpful support

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  5. Anonymous
    2022-09-12T20:05:39+00:00

    Well Said Thiru Vikkraman,

    Like if they dont know about it, instead they should find a solution once and for all

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