There's a fundamental contradiction between these statements: Sorry, but security is hard. If you want strong security, it won't be easy. You'll need to learn programs and possibly operating systems that you've never used before, and that might be twice as hard if you're a computer newb in general. I see these demands all the time. People want strong security but make it easy. They want bitcoins that are fast, cheap, and anonymous. You can't have the world. You need to pick a level of security that you are comfortable using and/or smart or dedicated enough to learn. Here's how I would break it down: No Security: You use TBB and PGP on an unencrypted hard drive. Everything you do can be discovered by an adversary. Low Security: All sensitive files are stored on an encrypted thumb drive, partition, or some other volume. This is low because the contents of such volumes can be leaked onto the unencrypted parts of the hard drive. For example, if you are a vendor who stores info in MyDrugClients.txt and you open that file in Notepad, the path and file name will be stored in the Recent Documents list. An adversary can discover the kinds of info stored on the encrypted volume and that alone can get you in trouble. The other problem is that you are still using the malware and shit infested Windows operating system. Microsoft cooperates with LE and even provides tools for forensic analysis of its OS. Your next KB134235325 proprietary binary blob update could be spyware pushed to your computer on behalf of LE. Medium Security: A portable Linux distro like Tails or Liberte. Better, because they are open source, the developers don't work for a corporation that bows to government pressure, and they use isolated encrypted volumes that don't leak data. The trade off is that you get a lot of little annoyances with the weird filesystem layout, installing applications beyond the defaults that come with the distro can be a pain even for a seasoned Linux user (read the recent thread about getting bitcoin-qt runnin on Tails), and constantly having to reboot between sessions. High Security: A Linux distro installed on the main hard drive with FDE. It offers the highest security because nothing about your computer can be known to an adversary except the kernel used to boot the system. They can't even prove the computer belongs to you if you purchased it with cash from a Craigslist seller. The main trade off is that this is the costliest option, because you need to dedicate a computer full time for this purpose. If you are wedded to your current OS, you'll need to buy a second computer, which can cost over $100 even for a used one. Broadly speaking, those are your options. You have to choose how much time, money, effort, and brain cells you are willing to spend on your security.