Outlook 365 for Mac - not sending attachments

Anonymous

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?

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240 answers

Anonymous

2022-10-11T13:56:55+00:00

Went to Beta chanel, found 16.67. Send an email with S/MIME cert and PDF attachment. This time it was delivered. Strange behavior. I've seen posts of others who say that randomly attachments were sent with previous versions. Interesting observation with 16.67: I have a signature including a logo (PNG image) it wasn't delivered either before. But now the logo is in the signature and in addition to the PDF I sent attached as separate file.
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Anonymous

2022-10-12T05:24:52+00:00

I would suggest that everyone who has not already, to open a ticket or contact support from with in outlook.
Maybe if lots of us submit tickets, maybe we will get into their radar to prioritize fixing this

The but still is in Investigating status, so I guess they still trying to figure out what is happening
Outlook fails to send attachments and inline images when sending a signed or encrypted email using the new Outlook for Mac (microsoft.com)
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Anonymous

2022-10-12T19:32:06+00:00
I created the following meme to express the frustration of many here:

All humor aside, there are two very acceptable work-arounds posted on this forum:
1. Roll back to the Legacy version (Help > Revert to Legacy). This is preferred.
2. Roll back to version 16.62 or earlier (there are instructions and links posted to download this version, then just drag Outlook to the trash and install it. Turn off updates and presto.
I've done this for the handful of people that work at the company I work for with 100% success.

Update: option 2 does not always work, perhaps need an older version, note the original post mentions the issue with 16.62.

Now it will be interesting to see how long it takes Microsoft to fix this f-real!
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Anonymous

2022-10-13T09:59:17+00:00

Could you please help me with the download link for rollback to 16.62? I'm desperate since with 16.67 Outlook asks me permanently to enter password and 2FA code for all MS365 accounts, even in legacy mode. Entering credentials without error message but no avail, pops up again and again. Deleting all Exchange, ADAL and office entries in keychain didn't solve the problem.

You are right saying using Outlook on Mac is nothing but a pain. Thanks!
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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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