Problems with responding to encrypted mail on alternative mail provider to 0365

[morgan2309]

Hi all,

We've recently began using 0365 OME function, creating rules to ensure mail to certain domains etc sends with automatic Encryption. The function works great outbound but outside orgs that are on different mail providers cannot reply to the encrypted mail, opening the mail is fine but an error showing 'Error: the message can't be sent right now. Please try again later' is showing when trying to respond via encryption.

This has been tested many times and were still getting the same error. Is it possible to set up an Encrypted connection to ensure the mail trail is encrypted both ways? 

[#2]

Hello, I've tried to reproduce this issue. First I'm sending an OME encrypted email to a Gmail account. I can reply directly from the wrapper email as well as when going to the OME portal via "Read the message" button.

I've also created a rule in EXO that uses OME with "Apply Office Message 365 encryption..." that automatically encrypts the email and in this scenario the Gmail account can also reply directly from the wrapper email or when opening it from the OME portal.

Can't say what you've missed here but it does work pretty seamless from my point of view.

Perhaps you need to look at the underlying config.

https://docs.microsoft.com/en-us/microsoft-365/compliance/ome-faq?view=o365-worldwide