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I'm looking for options for encrypting files on Windows that can be run portably. It looks like gnu pg may do what I want but I can't find a recent portable version of it. I do not believe Truecrypt is what I'm looking for since I'd like the ability to transfer encrypted files with out having to dismount and copy a truecrypt volume. My understanding is that copying Truecrypt volumes in use has some security implications. If it is an option I'd prefer a tool that can be used from the command line but I'm not picky.

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The other option I would recommend is FreeOTFE. But you'll have to essentially use their version of a file explorer. Just drag the files into the portable app's window and it gets loaded on. In operation, it feels like a glorified zip file, yeah. But at least no one can see what's inside.

Anyway you slice it though, I haven't found an applicaiton that is going to bring native handling with a portable application because that apparently requires administrative privileges.

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I'd like the ability to transfer encrypted files with out having to dismount and copy a truecrypt volume

You can keep the encrypted volume on your portable drive, as well as a portable copy of TrueCrypt. You don't need to copy and paste the TrueCrypt volume back and fourth. You can mount the volume directly off of the drive, and copy your files into the mounted drive. The files will be directly written to where the TrueCrypt volume is located.

I only bring this up because I highly recommend TrueCrypt for this sort of thing, as that's what it was designed for. You can also use it from the command line if you want. The only caveat with TrueCrypt is that it requires administrative privileges.

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If you just want to protect a few small files and don't need to access them in realtime, consider using KeePass 2. It's meant for storing passwords, but you can attach files to records as well. No admin privileges required.

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