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Truecrypt do not allow this (yet).

There is another cool utility - encfs. It have magic option "--anykey". Basically, it stops verification of key hash and always tries to decrypt with key you provided. Thing is - it will show you only correctly decrypted files. So, by using different passwords you essentially create layers of encrypted files, where each layer is decrypted by different password..

Truth is - if something did not decrypt, LEO will see it, but I do not see how they could prove you provided wrong password intentionally, and not at some point changed password to new one, and old been forgot. This essentially will happen when you use different password - you will receive no error and empty container where you can start add personal files..

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