Problems replying to encrypted e-mail

S

smackboy1

I'm using Outlook 2007 on a Vista machine.

When I receive an encrypted e-mail and try to send an encrypted reply to the
sender, I get an error message "Microsoft Outlook had problems encrypting
this
message ... recipients had missing or invalid certificates, or conflicting or
unsupported encryption capabilities". My options are to send the reply
unencrypted or cancel. I figured out that the problem is that when I hit
"reply", Outlook is not recognizing the e-mail address in the "To:" field as
a person in the Contacts who has a valid digital certificate. If I hit the
"To:" button and choose the person's name off the Address Book, then bingo,
Outlook figures out that the e-mail address has a digital certificate and
sends off the reply encrypted. So I know it's not a problem with an invalid
cert.

e.g. When replying to a clear text e-mail from someone in my Contacts, the
name in the "To:" field appears as "James Smith <[email protected]>". But if
the same person sends me an encrypted e-mail, when I hit "Reply", the entry
in the "To:" field is just "(e-mail address removed)" and when I click "Send", it
gives me the error message. If I right click the e-mail address I can "Look
up the Outlook Contact" but for some reason it doesn't recognize the digital
cert.

Why is the e-mail address not being linked to the Contacts info and how to
fix this problem?
 

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