Outlook 2016 Email encryption issue

Michael Miller
Michael Miller used Ask the Experts™
on
I have multiple users that when trying to send an email encrypted they get the error following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities.  One of the users is me however some users can send me encrypted emails.

If the person sending the encrypted emails search for me , right clicks , and adds me to his contact list he then is able to send me an encrypted email. I know this is not normal they should just be able to click reply with out adding me into contacts.

Any ideas?
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Top Expert 2016

Commented:
to send s/mime encrypted mail you need the recipients public key and the recipients need your public key
David FavorFractional CTO
Distinguished Expert 2018

Commented:
Reading your question my first thought was S/MIME as David Johnson suggested.

And maybe I'm guessing incorrectly.

Let's be clear if you're talking about....

1) True message encryption, as David Johnson suggested.

2) Opportunistic TLS which encrypts SMTP connections.

Mention which of these are correct.

Author

Commented:
Yes you are both correct.

However users get the error : Microsoft Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities.

If you go to the address book , right click on the user in the address book  and choose to add to contacts. In the contact you can see the user has certs published. if you choose to Save and close ( adding the user to your contacts) the error message goes away and they are able to send the encrypted email to the user.

This is only for a few users not all users are affected.

It is something in the network?


Thank you

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