S/MIME Encryption Troubleshooting Tool

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I=92m looking for an application that will help me troubleshoot S/MIME
email encryption issues. Specifically, software that looks at an email
or .msg file and outputs the applicable encryption certificate(s).  I
routinely troubleshoot email encryption issues in my organization and
a tool like this will help tell me identity why the recipient cannot
decrypt the email. Thoughts/suggestions?

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