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
    2022-11-16T17:07:13+00:00

    It's not fixed though, as multiple people have said.

    https://support.microsoft.com/en-us/topic/outlook-fails-to-send-attachments-and-inline-images-when-sending-a-signed-or-encrypted-email-using-the-new-outlook-for-mac-5719ab3c-70cd-4e19-8025-e51b7e055efa

    ..may say it's fixed, but it isn't, at least in my experience. I am using the latest version of Outlook (16.66.2 22102801) and the latest version of macOS (13.0.1) and when I send attachments in a signed email all that appears on the other end is a .p7m file - my signature. The attachments are not received.

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  2. Anonymous
    2022-10-19T20:52:13+00:00

    I am on 16:66 and am still experiencing the issue as of an hour ago. Just reverted to legacy and I was able to send the same attachment without issue.

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  3. Anonymous
    2022-10-13T18:27:58+00:00

    News Flash!

    According to Microsoft this is fixed with version 16.66, see:

    https://support.microsoft.com/en-us/topic/outlook-fails-to-send-attachments-and-inline-images-when-sending-a-signed-or-encrypted-email-using-the-new-outlook-for-mac-5719ab3c-70cd-4e19-8025-e51b7e055efa

    Wait! I know that several people here still report the issue with 16.66 and 16.67 (on the beta channel).

    Any comments from anyone who has tested this further? We had two people who had not switched to "Legacy" Outlook that one worked, the other didn't.

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  4. Anonymous
    2022-10-13T16:14:15+00:00

    From jbitschMMKDIGITAL's post a couple months back:

    For the affected users, downgrading to 16.62 has fixed the issue. You can download that version here: https://officecdnmac.microsoft.com/pr/C1297A47-86C4-4C1F-97FA-950631F94777/MacAutoupdate/Microsoft_Outlook_16.62.22061100_Installer.pkg

    Note: Copy-paste the above link as clicking it fails.

    thanks to homebrew-cask for keeping a version history :)

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  5. Anonymous
    2022-10-11T13:20:10+00:00

    16.67 (22101000)

    11 Oct 2022

    doesn't appear to be fixed.

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