Digital Certificate Problem

Posted on 2010-08-30
Last Modified: 2012-05-10
I have a user that received a digitally signed email and he would like to begin exchanging encrypted email with the sender.  The red certificate ribbon displays in the upper right corner of the opened message and everything checks out ok in the details of the certificate.  When I try to add the sender to the user’s contacts and save the certificate there isn't one under the certificate button.  I've tried adding it manually but the sending or receiving of encrypted mail fails.  Another user within my organization received a digitally signed email from the same sender and successfully added the certificate through the "save contact" button.  I've since had the sender send digitally signed messages to several other people and the problem seems to be about 50/50.  Some can see the certificate but others can't.  All users are on Outlook 2007 and an exchange server is being used.  Thanks!  
Question by:RandomIT
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Expert Comment

ID: 33559527

Author Comment

ID: 33559641
I can open the signed message in OWA but the Certificate is greyed out with a yellow exclamtion mark over it giving the error of "Revocation Check Failure" The validity of the digital ID can't be determined because the server that provides this information can't be contacted.   The certificate is issued by DOD Email CA-20.

Expert Comment

ID: 33561377
I would contact the source to make sure they are publishing their CRLs appropriately.  Also, do all the machines in your organization needing this have the DoD RootCA installed and enabled on their systems via the Windows Certificate MMC?

Author Comment

ID: 33562834
The CRL option would make sense if no one could save the certificate but it appears to be random as to who can and can't see and save the cert.  I've also downloaded and installed all the DoD Root CA's and the certificate still doesn't show up.
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Expert Comment

ID: 33567939
This process would add the recipients public key to your system which may resolve the issue.

1.Open a message that has been signed.
2.Right-click the name in the From box, and then click Add to Outlook Contacts on the shortcut menu.
3.If you already have an entry for this person, click Update new information from this contact to the existing one.

The certificate is now stored with your contact entry for this recipient.

To view the certificates for a contact, in Contacts, double-click the person's name, and then click the Certificates tab.

Author Comment

ID: 33568250

The process you outlined is the one we've been trying to get to work.  The issue comes into play when we try and add the sender to the contact list.  Everything shows up correctly within the Contact preview but when we click on the "certificate" button there is nothing listed.  This same screen is where we've tried to "import" and the it still doesn't work.  

Accepted Solution

MONSTA2008 earned 500 total points
ID: 33583363
Does this same behavior occur on the same digitally signed message received by someone who can vs.  someone who can't view the recipients certificate?

Have you also tried manually downloading the DoD CRL to a problematic system to see if that resolves the issue?  You can get the CRLs for DoD CA-20 here:

Author Comment

ID: 33588238
Thanks for the good advice Monsta2008.  I've downloaded both items and imported them.  The OWA now sees and accepts the certificate as valid.  The certificate still doesn't show up in the Contacts option though.  This is definitly progress though.  Thanks!

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