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The author examines the debate about Microsoft's Passport technology--it will be difficult to design a workable Internet identity framework. Were currently trapped between Scylla and Charybdis. On one side, civil libertarians warn that a centralized authentication service comprising a concentration of power and operational and systemic risk represents an unacceptable threat to a free society. On the other, we have a chaotic morass of idiosyncratic user ID and password implementations that inconvenience people and invite attack.