I was indeed oblivious to the idea that VPNs might have a hard time working together with other DNS servers. Through trial and error I actually found out, that my so beloved plan looked actually like this:
All I knew was what a VPN was and how to make use of it. What I chose to ignore was the other side. What I wanted to do, wasn't too complicated. Thus, I didn't do as much research, not knowing much about the topic at that time, and chose a VPN provider that seemed sound and simple to use: Tunnelbear. Now I do admit that back when I first learned about VPNs, I simply wanted to use one myself – if only for the additional security in LAN settings. I rely on VPNs all the time, thus, it was essential to me. While I thought that was it, the real challenge was getting it DNSCrypt to work with my VPN. The idea being, that DNSmasq caches your DNS queries and DNSCrypt encrypts all of them, essentially giving you more anonymity. In the last post I showed you how you can use DNSmasq and DNSCrypt together on a Mac. As this is one of those trials, where I hoped that it's not completely my fault, but in the end, it turns out that it is.
