Tails doesn't have persistent entry guards. This is a *major* anonymity vulnerability and puts you at a *much* higher risk of being deanonymized by even fairly weak attackers, particularly if you use it for an extended period of time. If you boot tails once a day for a month your risk of being deanonymized by an attacker engaging in a profiling attack is about the same as it would be had you used Tor with persistent entry guards for two and a half years. If you want to be as likely to be deanonymized by a profiling attack in a month as I am in two and a half years feel free to keep using Tails. IMHO Tails is actually probably more of an asset to people who want to trace Tor users than to people who want to avoid being traced. It makes it very easy for its users to greatly increase their vulnerability to one of the most dangerous and widely known attacks against the anonymity of Tor users. And it does this while acting like it is a security focused distro. In all honesty it isn't even that impressive of a configuration, even if you ignore the absolute deal breaker that it doesn't have persistent entry guards. It is a security toy with critical flaws in it. That it is suggested by the Tor devs is absolutely stupid, particularly since they will be the first to admit that it indeed *greatly* decreases user anonymity if it is used how it is intended to be used (as a live CD and not loaded from a persistent state via snapshots or similar). They may not admit that it is a security toy though, but it really isn't at all the ideal configuration. The only place Tails has in your security kit as for use as a live CD if you use random WiFi access points and don't want your sessions to be linkable to a single entity via the fingerprint your entry guards leave in the logs of the WAP (not many people use the same combination of entry guards, so by using that combination persistently you essentially leave a fingerprint at every WAP you use that will allow for an attacker to link all of your sessions to one entity). That is the only advantage of not having persistent entry guards, and for probably 99% of people using Tails it is entirely outweighed by the extremely real risk of reducing your protection from profiling attacks and making it *much* more likely that a given attacker manages to trace one of your Tor sessions to your actual location. Decide what is more important to you I guess, not having WAP sessions linkable to each other based on entry guards (btw you better also be using a MAC address randomizer between every session, in addition to some other things, or your sessions will be linkable even without an entry guard fingerprint) or not having your location traced in the first place. If your security requires that you physically hide things you can rest assured that your security is absolute fucking shit. Hiding flash drives is suggested as a security technique by (estimated) 0% of security experts.