Hello all!
I am using Outlook 2013 with both Exchange Online (Office 365) and with an IMAP server. The accounts are configured to use two completely separate profiles as Outlook isn't able to handle multiple S/MIME certificates (ahem! FEATURE REQUEST!!! ahem!). LOL
I have actually been having this problem for a long time and none of the KB articles, blog posts, or 3rd party websites seem to address the issue I am experiencing.
My requirement is to send and receive encrypted e-mail from a group of external recipients. I have valid certificates from each of the recipients and have gone through the painful process of creating individual Contacts for each recipient, then associating the certificates with the respective contacts.
For whatever reason, I am able to send encrypted e-mails to some of my Contacts without issue, but with others I am not. The results are very inconsistent despite the fact that I have all of the Contacts configured in an identical fashion.
The message I receive is probably familiar with most:
Encryption Problems
Microsoft Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities:
Username 1, Username 2, etc.
Continue will encrypt and send the message but the listed recipients may not be able to read it.
"Send Unencrypted""Continue" (ALWAYS GREYED OUT)"Cancel"
I have deleted the Contacts and re-created them, I have deleted the Auto-Complete address list for inline auto-complete, I have even tried deleting the profile and re-creating it from scratch. I have also gone into the Certificates MMC snap-in and tried adding the certificates for the users there. Still I receive the same error.
This happens regardless of whether the mail server is Exchange (and Publish to GAL is enabled along with custom Mail Contacts), or it is IMAP/POP3/Gmail/etc.
What is the best way to debug this issue? There doesn't seem to be any sort of advanced logging, that I am aware of, which would allow me to see what the exact issue is. It's very frustrating because other e-mail clients, such as Mozilla Thunderbird, work just fine with the same recipients. But I hate Thunderbird and don't want to use it if I can avoid it.
Even Outlook 2011 for Mac OS X works just fine, but Outlook for Windows (2010 and 2013) do not.
I'm about to open a support case with Microsoft Support, but wanted to ask the Microsoft "wizards" here if there are any other options I can try to enlist to resolve the issue on my own.