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
    2022-09-03T14:54:29+00:00

    Sounds like your observations are exactly the same as mine! I deleted the Outlook version for Mac 16.64 from my applications folder and replaced it with version 16.62. Since that time the problem has disappeared!

    I will not update any of my Office 365 applications fro Mac until I have had explicit confirmation from Microsoft that they have removed all bugs from such new Office suite version.

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  2. Anonymous
    2022-09-04T06:35:04+00:00

    This is a known and confirmed issue when using Google Workspace and new Mac Outlooks. All versions have the same issue.

    @Microsoft can you please do a proper investigation and bug fix. It is extremely annoying when a basic functionality is not stable.

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  3. Anonymous
    2022-09-08T11:18:32+00:00

    I'm also experiencing this issue with multiple users in our org, not all of them though. They're all running most recent macOS (12.5.1) with most recent Outlook (16.64). 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, thanks to homebrew-cask for keeping a version history :)

    @Microsoft: this issue is unacceptable. This behaviour is *very* misleading for users as it silently fails to add the attachments and doesn't even display an error. Please fix this as soon as possible, I don't like being stuck on an older version...

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  4. Anonymous
    2022-09-08T12:26:14+00:00

    Same here. Intermittent issue with attachments which are visibly attached before hitting send not actually being sent and not showing up as attachments in the same email once it is in the sent folder. This doesn't seem to happen when I shelve the attachments in Dropzone and then attach from there.

    This is a huge issue when sending time sensitive legal documents!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

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  5. Anonymous
    2022-09-08T18:21:47+00:00

    I've been having this issue for weeks. Files will show as attached when drafting a message, will show as attached even when pressing send, and then when I check my sent folder it turns out the file was not attached. Not sure if this is Mac related, or because I'm using a Gmail based account.

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