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Exchange 2010 and Outlook 2010 Encrytion problem

I have 5 different users and all but one can send and receive encrypted emails.
This one person can send encrypted emails to all 4 people and they can read the emails.  He just cannot read any of the encrypted emails we send him.
I have gone through the whole process of sending a signature and then adding each user into his contacts.  I can also verify when he sends an email and you view the Contact properties it has the correct Cert for that user installed.
He gets the "Cannot open this item - Your digital ID name cannot be found by the underlying security system" when trying to open our encrypted emails.
I have tried the following with no luck
1) Replace Cert with a new one.
2) Removed option to use "Cached Exchange"
3) Removed Mail profile and created a new one with a new Cert
4) logged into another computer and created a new profile and imported his Cert.pfx

Always the same result.

Since I did a complete new setup on another computer I get the feeling it is either Exchange or our Cert Server.
1 Solution
Simon Butler (Sembee)ConsultantCommented:
Instinct says account or as you say, your certificate server.
I would suggest a new account as a test, do the certificate work and then see what happens.
If the new account works correctly, then you will have to migrate the user to that new account.

I would suggest that you do a forward on the old account to the new account so that everything inside Exchange works correctly.

djpierce54Author Commented:
I did perform that test and the new account works flawlessly.
I will go ahead and do the migration as it would be a huge time synch to try and troubleshoot where on the server the problem is occuring.

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