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Submission + - Secure chat+file transfer software for Winxp?

Tinfoil Hat paranoid writes: Recently I've found the need to establish encrypted chat and file transfer with people over the country. Since we're dealing with very sensitive data (there are corporate interests involved), we need the connection to be as secure as possible — if can be anonymous (hiding our IP addresses), even better, but it's not mandatory. What Windows software do you recommend? We need something *VERY EASY* to install/configure (think 1-click), that also allows us to resume interrupted file transfers. I wouldn't mind paying a few bucks, but generally I don't trust closed source products. What secure chat/file transfer products have you used, and what are the pros/cons of each?
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Secure chat+file transfer software for Winxp?

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To do two things at once is to do neither. -- Publilius Syrus