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Yeah, I was unsure how the fifth amendment related to this. But let's say fifth amendment is not an issue -- say, police suspects that my encrypted file contains evidence against my friend Bob. They'd need a court order to compel me to decrypt the file, no?

Most definitely. Like you said, the fifth amendment protection would likely not apply then. You might make the argument that the fact you had evidence of a crime in some way incriminates you I suppose.
 
Most definitely. Like you said, the fifth amendment protection would likely not apply then. You might make the argument that the fact you had evidence of a crime in some way incriminates you I suppose.

[armchair-lawyer] This gets into blurry areas. If they ask you if you have any evidence you can either lie or tell the truth. Lying creates its own set of problems obviously, if they can later prove that you knowingly lied.
If you say you do have it and they ask for it, then refusing to give it to them is another possible bundle of problems that probably gets into obstruction of justice. About the only likely way out would be if that evidence would also incriminate you, thereby triggering fifth amendment protection and the end result would likely be some sort of grant of immunity in exchange for providing the evidence. [/armchair-lawyer]
 
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