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I've got serious problems with Outlook for Mac 2016 and S/MIME.
If I import the certificate of the recipient manually from the AD into an Outlook contact (or from a previously received message), Outlook 2016 is able to send the email encrypted without any errors.
If Outlook is searching the AD for an unknown recipient (that is not within my local contacts list), it finds the correct certificate but afterwards I'm always getting the error message "Message could not be saved" and the email can't be sent or even saved as draft. As soon as I remove the S/MIME encryption the message can be sent.
More details also available here: https://community.office365.com/en-us/f/153/t/359082
Using older versions of Outlook for Mac in business environments
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.
Answer accepted by question author
A quick test just now with 15.15 (151008) looks very promising. I did not get the error, which is usually very easy for me to create. What about you?
Many thanks for the info!
As soon as I get the update, I will post the results here.
I guess this is as "official" as it gets:
Hello everyone, I am a program manager on the Mac Outlook team. We have identified and fixed this issue and the fix will be available in the next release of Mac Outlook, which is scheduled for sometime early Sept. Thanks for your understanding and patience regarding this issue.
https://community.office365.com/en-us/f/153/t/401642?pi14985=2
So I guess we have to wait some time more...
We encountered this problem last week, so within the next weeks this should be solved.
Unfortunately I can barely get hold of the affected Mac client in our company so if you could share any updates on this topic here, that would be great! :)
I did this already, but it would be great to get an official response from Microsoft if and when they plan to fix this issue.
Mail encryption does have issues in the new version of outlook. It has already been reported earlier by many users. Have not found any update from MS with it. You can too provide feedback on the same by clicking on the smiley icon.