Tailscale

Tailscale has become an absolute game-changer for my workflow. I rely on Remote Desktop for Windows-based tasks, but my Wi-Fi in certain locations is barely functional. With Tailscale, that limitation disappears. I can put one device on cellular, keep my main machine on home Wi-Fi, and Tailscale stitches everything together through its own encrypted mesh network. Because it builds a secure WireGuard-based overlay, every device feels like it's on the same LAN —even when they're on completely different networks. As long as my devices are online, Tailscale maintains the connection flawlessly. No port-forwarding, no VPN servers to babysit, no weird NAT issues. It just works, and it's shockingly reliable. The flexibility is enormous: remote access, file transfers, RDP, SSH, ad-hoc services, subnet routing, exit nodes—you name it. Once you start using Tailscale, the number of things you can do with it feels practically limitless.

tl;dr - if using for pihole ad blocking outside of home network, just install AdGuard DNS profile to your iOS device(s). Way easier, no need for an extra app, blocks ads. Idk why I tried complicating something that has worked for me for years and years. Followed kb instructions to a T. I’m not new to things like this. Installed tailscale on my headless pihole (went the the url at the end of setup too), opened pihole to outside traffic, changed the tailscale DNS settings to point to my pihole IP address, added the VPN profile to my phone. According to the documentation everything should’ve worked. Both my iPhone and pihole showed in the settings. Zero ads blocked. I have 3 separate domain blocking lists configured on my pihole.

App has definitely gotten better with updates and so I’m thankful for that. Not that long ago I had to force quit the app a few times to finally get it to connect and not give me re-auth errors. However, battery life and management is still a very very big deterrent to using this how I originally wanted to, which is always-on, using my pi-hole server for DNS and ad blocking. I’m following the issue in GitHub. Please please fix! Many users seeing the same thing and providing dumps. If you guys can get the battery usage under control then the app will be UNSTOPPABLE.