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The best rule of thumb is... don't say anything on IM or email that you wouldn't say aloud in the middle of a crowded room. Even if your friend came up with some ultra secure fashion for communication to his router... your IM is still travelling over the open internet. AIM, MSN, Yahoo, Google Chat - none of them are secure messaging. Some corp solutions are (encrypted TLS/MTLS connections all the way) but the free ones aren't...
Jason
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A computer once beat me at chess, but it was no match for me at kick boxing.
-- Emo Philips
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