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At the moment I try to move ~350GB of data into a truecrypt partition via Windows Explorer on Windows Vista. Unfortunately the data transfer breaks down frequently. Is there a workaround? Should I use another way to transfer the data than Windows Explorer? If so what would you recommend?

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Robocopy is your friend. There are numerous alternatives, but robocopy is included with Vista and should work fine for your purposes.

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RichCopy is an improvement of RoboCopy...technet.microsoft.com/en-us/magazine/… – Moab Mar 2 '11 at 22:01

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