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Link: Peter Gutmann on PKI
Everything you never wanted to know about PKI but were forced to find out [PDF] by Peter Gutmann is a set of slides about just that: a pile of the warts and issues with PKI in general and the SSL model in specific. If you're interested in the whole field, his home page has links to enough additional papers to keep you reading for some time.
(From Chris Samuel, and that in turn from Russell Coker.)
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