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I have an Exchange 2013 environment that I'm trying to implement S/MIME with smart cards. To the best of my knowledge, and the little help I have received on TechNet, I have configured my Exchange server correctly. I have installed the S/MIME controls on a Windows computer, I am able to log into OWA with a smart card, but when I try to sign an email or tell OWA which certificate to choose for digital signatures, nothing happens.

Has anyone successfully signed or encrypted an email using a smart card with OWA 2013, or have any ideas about what might be causing this problem?

HopelessN00b
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wolfenstein87
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1 Answers1

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I found the problem. First, the Signing cert was missing Email Protection EKU. Second, the emails need to be sent as plain text. I have yet to find the document that states the users emails must be sent as plain text for this to work in a browser, so if somebody comes across it, please enlighten me.

wolfenstein87
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