Exchange 2010 and Outlook 2010 Encrytion problem

Posted on 2012-09-07
Last Modified: 2012-09-13
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.
Question by:djpierce54
    LVL 63

    Accepted Solution

    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.


    Author Closing Comment

    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.

    Featured Post

    Free Trending Threat Insights Every Day

    Enhance your security with threat intelligence from the web. Get trending threat insights on hackers, exploits, and suspicious IP addresses delivered to your inbox with our free Cyber Daily.

    Join & Write a Comment

    Learn more about how the humble email signature can be used as more than just an electronic business card. When used correctly, a signature can easily be tailored for different purposes by different departments within an organization.
    Not sure what the best email signature size is? Are you worried about email signature image size? Follow this best practice guide.
    The basic steps you have just learned will be implemented in this video. The basic steps are shown to configure an Exchange DAG in a live working Exchange Server Environment and manage the same (Exchange Server 2010 Software is used in a Windows Ser…
    This Experts Exchange video Micro Tutorial shows how to tell Microsoft Office that a word is NOT spelled correctly. Microsoft Office has a built-in, main dictionary that is shared by Office apps, including Excel, Outlook, PowerPoint, and Word. When …

    745 members asked questions and received personalized solutions in the past 7 days.

    Join the community of 500,000 technology professionals and ask your questions.

    Join & Ask a Question

    Need Help in Real-Time?

    Connect with top rated Experts

    15 Experts available now in Live!

    Get 1:1 Help Now