Just wondered if anyone had successfully got Google Workspace Gmail and Outlook 2016/365 Apps for Enterprise playing nicely together for S/MIME encrypted emails?
Digital signatures work all ok in both directions, encrypted emails work for most use cases also except when the email was encrypted within Outlook and then you're trying to open it within the Gmail Web UI (works fine in the opposite direction or between the same clients).
My only theory is that Gmail Web UI uses and therefore expects encrypted emails to also be digitally signed after encryption (which is more secure) where as Outlook doesn't seem to do this and only encrypts. You can see the different headers - doesn't seem to be an option in Outlook to force different behaviour or within Gmail to accept lower security. (This is only my speculation though-could be wrong!)
Just wondered if anyone had come across this or could offer any insights? Pulling our hair out a little! 🙂
Anyone got this working seemlessly between different email clients?