Running Tails in a VM defeats the two main advantages of using Tails. 1. Leaving no trace on your computer. If you're running it in a VM, then the system image is on your hard drive. The reason most people want to use Tails is so they can put it on a thumb drive that is easily destroyed, swallowed, flushed down the toilet, etc., leaving no trace of Tor activity on their computer. If the shit hits the fan, you won't have time to properly wipe your drive or that file. 2. It's based on Linux, so the attack surface for malware is much smaller. Assuming Windows is your host operating system, your Tails VM is potentially vulnerable to the malware that infects Windows. If you're going to run something in a VM, you might as well run Whonix, which isolates Tor in a separate VM and gives you a little better security, although you need to store the images in an encrypted container, or install a custom Workstation with full disk encryption, because unlike Tails, data is stored unencrypted in the default Whonix Workstation. Unfortunately, Whonix hasn't been updated in 6 months and the Gateway VM still uses Tor 0.2.3, and upgrading it to Tor 0.2.4 seems to break the Gateway for a lot of people. I haven't explored it enough to figure out what the safe upgrade path is (ie, which changes should be accepted and which shouldn't during the upgrade), although I did get Tor 0.2.4 working in the Gateway before. Expect Whonix to be slow with Tor 0.2.3 because of the botnet. OTOH, the latest version of Tails upgraded to Tor 0.2.4, so kudos to them. The main problem with Tails is the lack of persistent entry guards. That should be TODO item number one. I don't know why it isn't. You should manually set bridges to get persistent entry guards. BTW, Tails isn't the best way to browse SR. Take a look at this thread: http://dkn255hz262ypmii.onion/index.php?topic=201622.msg1448383#msg1448383 In the two months since that thread was started, a paper came out about external passive surveillance of the Tor network, http://dkn255hz262ypmii.onion/index.php?topic=209514.msg1512060#msg1512060 and we've learned a lot about massive surveillance by intel agencies. These revelations have changed the game, imo. I honestly don't know what to tell you now. Tor may not be sufficient to protect you against near-global surveillance by cooperating intel agencies. It seems that all low latency anonymity systems are fucked. The Tor Project web site admits as much, right on the main page: "For most uses, Tor provides the best available protection against a well-resourced observer. It's an open question how much protection Tor (or any other existing anonymous communications tool) provides against the NSA's large-scale Internet surveillance." The people I talk to who know a lot about anonymity systems seem to think that high latency mix networks are the only way to get anonymity in the face of this surveillance. The only thing I can tell you in the mean time is to tunnel out of and/or avoid the countries with the most aggressive surveillance.