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I have been asked by a relative to encrypt both a USB pen & a Hard-disk folder. My immediate thaught was to use Truecrypt being that its free and relativly decent!

My question is this: is there a way to enter the decryption-password and decrypt both the pen AND the hard-drive volume at the same time? Obviously the solution should hopefully work if the USB Pen is not present or the USB pen is being used in a seperate computer.

Having not used Truecrypt before in anger I would be grateful for any assisstance.

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TrueCrypt has an option to cache the encryption password. If you check it when entering the first password, TrueCrypt will try to use it for future volumes.

For example, my login script looks kinda like this: (converted from Python)

truecrypt /volume foo.tc /letter p /auto /quit /cache y
truecrypt /volume bar.tc /letter q /auto /quit
truecrypt /wipecache /silent /quit background
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Wouldn't this be unsafe (kinda loosing the advantage of the password in the first place)? I trust TrueCrypt to not give unsafe options, so there must be more to this... – nik Oct 9 '09 at 12:02
The cache is only stored in memory, and in my example wiped at the end, using /wipecache – grawity Oct 9 '09 at 12:42
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