If I send a message with an attachement, I get asked what encryption
scheme I want to use for that message. PGP/MIME is ideal, and there's no
reason not to, if we can assume that the recipient's client supports it.
Why not perform a check of the headers on all of the previously received
mail from the email address you're presently sending mail to, and then
skip the attachment scheme selection dialog if the contact's mail has
been exclusively composed either on mail clients that support PGP/MIME
or on ones that don't?

Perhaps we should just send all mail by PGP/MIME _unless_ the
recipient's address is on a cached blacklist that can be maintained by
analyzing all incoming mail and adding an address to it whenever a
message is received with a client header indicating that the recipient
contact uses at least one client that doesn't support PGP/MIME.

Thoughts?

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