I’m playing around with Tailscale, but I’m not sure about the privacy aspect of being on a VPN all the time. I want to sync DEVONthink and OmniFocus using a WebDAV server on my Mac mini, but running Tailscale 24/7 raises some questions.

  1. Is it really end-to-end encrypted?
  2. Does all traffic go through the VPN?
  3. What about network issues when using a VPN? I’ve seen some connection drops in the OmniFocus sync logs when I used my Mac mini as a sync server.

I love the idea of having my private network of devices available everywhere. But I don’t trust random companies with my data, so I want to do my research before I start to use Tailscale with all my devices.