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IIS 7.5 - Client Certificate not trusted

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I have a web service that my customers connect to that requires self-signed client certificates to identify the user.  It works for all of my customers except one.   When I load their certificate into the Trusted Root Certification Authorities (machine store), IIS still does not trust it.  This is not a problem for my other customers.  


I have 15 customers and only one has this issue.  All of the other customers' certificates are trusted without issue.  I can verify the certificate in question is not being passed in the CRT using OpenSSL.  Negotiate Client Certificates is enabled (using netsh http add sslcert.)

I have tried iisreset, getting the customer to create another certificate and setting the purpose on the certificate in the Trusted Root to Client Authentication.  Is there anything else I might be missing?  Is there a way to "refresh" the CRT IIS is sending out without having to create a custom CRT?  I have a feeling it may be the tool they are using to create the certificate but I want to rule out as many possibilites as I can on my end.


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