Replying encrypted to incoming encrypted e-mail? Send encrypted w/missing keys?
We've been using PGP Desktop since before it was called "PGP Desktop." For most encryption, decryption, signing and validation tasks it has served it's purpose. With later versions of PGP Desktop (10.0.2) and MS Office (2007), a few quirks and questions have started to pop up.
Replying encrypted to incoming encrypted e-mail?
According to one of my users, prior to her Office 2003 -> Office 2007 upgrade, PGP Desktop would automatically generate an encrypted reply to an incoming encrypted e-mail. This totally makes sense, since you'd want to keep the conversation private if it started out that way. I currently see no policy knob that would match on encrypted incoming e-mail and reply in kind. Can this be configured, and if so, how/where? As a workaround, we're using a policy match of message flag = Confidential.
Sending encrypted e-mail with missing public keys?
This same user had a need to reply encrypted to a received encrypted e-mail (see above), and was able to create a policy to encrypt if the message was Confidential. Unfortunately, out of four recipients, only two had PGP keys in her keyring. While fully appreciating the fact that the recipients without keys will not be able to decrypt the e-mail, is there any way to have PGP Desktop send the e-mail encrypted to those recipients with keys, and only fail to send to those recipients without keys?