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A few rules of thumb result from even cursory examination of the likely environment:
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5. Ultimately, the only way the remailers will provide what might be described as Pretty Good Security will be when we have software that maintains a regular or random rate of messages to and from the remailer cloud, a stream into which the meaningful messages can be inserted with no visible change in traffic. Until then, the best we can do is try to keep traffic levels up, and to send and receive frequently enough to frustrate end-to-end traffic analysis.
Well, the existing remailer net doesn't make "Pretty Good" anonymity very feasible. I'd think something based on the general idea behind Crowds. (Furthermore, most remailer structures still can't erase some other security concerns -- 1: remailers acutally can be hacked or physically compromised 2: clients really can be screwed 3: etc. To help solve the first, you'd want a two-box setup doing remailing, with the security-critical stuff loaded on a box not directly connected to the Net with something 140-1ish to make tampering harder, a secure OS, etc. -- or, of course, you can scrap all that to get really big remailer count. To help solve the second problem, there needs to be a better web-of-trust setup -- that is, one which applies to code as well as keys. Those who wish to verify code get a .sig-verifying program from a trusted source then use a WoT to authenticate various facets of the program necessary for security. A solution to the third problem is expected RSN.)
6. Don't send anything that can have grave consequences.
Remember the consequences to an adversary who uses its secret decoder ring, though: the more plausible it becomes that a certain source is being used for intelligence-gathering, the more likely it is that that source will promptly begin to run dry as the spied-upon realize that Something Got Broke. My advice, however, agrees with that of the other Anonymous. That is, unless you've really thought things out, think of an remailed message as merely .sigless, not anonymous.
7. Take names. Always take names. Some day...
FUDBusterMonger
It Ain't FUD til I SAY it's FUD!