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I’ve read this before, but it’s worth pointing to: Jon Udell on SSL Proxying.

the browser's secure traffic flows to Proxomitron. It decrypts that
traffic, so you can see it in the log window, and then re-encrypts it to
the destination server. Coming back the other way, it decrypts the
server's responses, so you can see them in the log window, then
re-encrypts them to complete the secure loop back to the browser.  It's
really quite amazing, and amazingly useful. Automation tasks that used to
look like more trouble than they were worth -- for example, driving a
HotMail or E*Trade account from a script -- suddenly look easy.