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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?
Using older versions of Outlook for Mac for personal email and calendar
Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.
as far as I could test, and from what I see on the other posts, it is only for SMIME (signed/encrypted) emails.
If you do not use one of the 2 you should be fine. Or at least this is what the behavior indicates so far.
right now I am on 16.66 and so far it looks good. I have only send about 10 emails but at least so far all of them had the attachments.
This is specific to users sending emails with digitally signed or encrypted emails. Is it relevant to those of us who do NOT send digitally signed or encrypted emails through Outlook?
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!
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)
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.