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Digital ID Outlook 2013

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I can't seem to get digital ids to work in Outlook 2013. I have a customer who needs to send encrypted messages to our e-mail address. We have a digital id that is used in Outlook Express 6. Other people use our id to encrypt messages back and forth just fine. Recently our client upgraded from OE6 to Outlook 2013. I sent them a signed e-mail, and had them add a new contact. The id DOES NOT get imported this way. I told them to manually import the id, which I sent to them as an attachment. They are able to import it, but the email is still sent in plain text. Somebody please explain the difference here. Why can't I get this to work

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