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Borrowing inspiration from May, a page from Scheier and some code from Gutman...
Hard disk space being cheap now, Bob creates several distinct disk partitions and uses Peter Gutman's Secure File System, or equivalent, to encrypt all of them. First, Bob fills all of them with innocous data. Next, Bob writes one or more partition with secrets. Bob arranges that no one knows the pass phrases for some of the innocous partitions by luring the cat across the keyboard or having his six year old punch something in while he is out of the room. Bob carefully and publically documents the fact that he did this without indicating which partitions
and how many partitions are actually useful. In addition to regularly using the secret partitions, Bob periodically updates the innocous partitions, who's pass phrases he does know, with more uninteresting but contemporary data.
When ordered to do so, Bob could reveal the pass phrases to the
innocuous data and to as much of the secret data as he felt necessary. Bob could not be forced to reveal all of the pass phrases as he does not know all of them. Naturally, the disk encryption routines would not store pass phrases but only a validating hash, that even Bob could not reproduce for all of the partitions.
Practically, Bob cannot be forced to reveal the pass phrases to any alleged remaining secret data, since this might not exist. To further encourage this belief Bob might associate innocous data with a first pass phrase, mildly embarrasing data with a second, and so on, and then, after revealing the first, gradually allow himself to be be coaxed into revealing the second and disclose a third only after the rubber hoses came out.
Since all of the partitions have similar content, no statistic should reveal which is which. Bob might have a bit refresher routine periodically nibble read and rewrite the whole disk so that no electronic characteristic exists that reveals record age.
No doubt, a judge might whimsically keep Bob in jail for a while, trying to assure that he has revealed all of the pass phrases, but the judge can never be certain, even when Bob has disclosed everything. This situation creates doubt that Bob is in contempt, even when he is, and makes a prison term relatively pointless, unless for revenge.