Outspring Mail observes the user's actions and learns from them, suggesting likely destination mailboxes for messages and even offering to use a previous reply to answer a frequently asked question. Outspring CEO Jeff Baudin said, "If I frequently reply to an email message that says, 'How do I get to your office?' or words to that effect; shouldn't my email program be smart enough to know I've replied to this same type of message before? And shouldn't it then offer to use one of these replies for the current message?"
But TidBITS pronounces Outspring Mail "a little rough around the edges." And Daring Fireball's John Gruber says it crashed on him a couple of times when he tried to launch it. And $95 is a lot of clams. So I'm not seeing anything that makes me eager to try Outspring Mail.