GPG was first written for Linux and later ported to Windows and OS X. Of course it exists for Linux. However, "GPGTools" is a port specific to OS X. Tails comes with its own GPG programs. https://tails.boum.org/doc/encryption_and_privacy/gpgapplet/index.en.html Well, if you never get a visit from LE, then it doesn't matter what you do. The whole point of security measures is to prepare for the worst case scenario. If that thumb drive isn't encrypted, your identity and activity in this community could be revealed to LE. Correct. Tails is designed to be booted from read-only media and save nothing on disk. There is an optional encrypted persistent volume. The Tor browser bundle doesn't store cache or browsing history on disk either, but if you save bookmarks or passwords, those will be stored on disk. There's no simple answer to that question, because people operate with different threat models and computing requirements. Some people share computers with roommates or go to libraries and they can't implement certain security features. Also, from talking to hundreds of people on the forum, I've learned that when people ask to be "most" secure, they really mean some optimal trade off between security and convenience. Are you using a 64 character password on your SR account? Well, why not? That's MORE secure than a 16 character password. The most secure would be whatever the hardcoded limit is for the password field, probably 256 characters. This feature is easy to implement, so if you're not using a max size password, you don't really want to be MOST secure, you want some convenience.