Thanks. Nice to meet you too. Have you tried to reboot and copy the .gnupg folder from the thumb drive back into your home folder, then start Kgpg and confirm that your key is there? You should do that before distributing it to other people, otherwise there will be much head aches and sadness when they send you messages you can't decrypt. It's an encrypted tunnel from your home to the VPN server. The ISP can't see that you're running Tor circuits through it. LE could ask the VPN to log your activity. The VPN can certainly see that your outbound connections are going to Tor relays. You can make that more difficult by getting a VPN offshore, especially in some shady country. You could make it even more difficult by getting a VPS in a different (shady) country and setting up a private bridge. Then your connection goes from home -> VPN -> private bridge -> Tor network. You could add as many proxies and hops as you want, but ultimately a determined adversary who can get each country / ISP to help, can follow the trail to the Tor relay. There's really no absolute way to hide your Tor use from a very determined and powerful adversary. You can only make it increasingly difficult for the adversary, and much less usable for yourself, with every hop. The bottom line is, you don't have to worry about that. 500,000 people connect directly to Tor relays every day, and they do so for dozens of reasons, many of them perfectly legal. Using Tor is not evidence of any particular crime, and it is extremely unlikely that LE could get a search warrant based on "this guy uses Tor", with no other evidence. They wouldn't even know what crime they would (potentially) arrest you for. Are you using Tor for CP, drugs, money laundering, hacking, stalking? Without evidence of a specific crime, or evidence to be suspicious of a specific crime, no judge is going to issue a search warrant. At least not in any non-despotic country.