Tails is based on Debian and Liberte is based on Gentoo. Both offer security hardened features that mainstream distros don't, such as scrambling RAM on shut down. Liberte uses a specially hardened kernel, too, though I don't know the details of that. The trade off is that these specialist "distros" are experimental and can be buggy. Windows GUIs don't have these advanced options in their interface. It's been a while since I've used GPG4Win, but it *should* come with gpg.exe, I know GPG4USB does. You can run these options at a command prompt.   gpg -v encrypted_msg.asc becomes   gpg.exe -v encrypted_msg.asc in whatever folder gpg.exe is located. Edit: I'm replacing what I wrote here before with my current recommended gpg.conf: You can, but it's too easy for newbs to fuck up and deanonymize themselves, or mix up their identities. It's better to extract GPG4USB in separate folders and use them separately. Name one folder MY ILLEGAL IDENTITY and the other MY REAL IDENTITY, so you absolutely don't mix them up. Oh, and don't name any folder "ILLEGAL" unless it's on an encrypted volume.