My Pi-hole is handling my DHCP, and I have Tailscale set up for remote access.

But how to I set my devices (for example, phone outside of my LAN) to route as follows: device > Pi-hole > NordVPN? Is that even possible?

The end goal being to combine the benefits of Pi-hole with a paid VPN, regardless of location.

Setting up the PiHole device as a DNS server & DHCP server still won’t make all traffic flow through it, you need it to be a gateway for all traffic that isn’t destined for an internal subnet.

To do that, you’ll need to set up your device as a router, with the necessary entries in iproute2 and iptables in order to keep lock out external connections without conntracks. You might be able to route to a turnkey container of some kind.

Is there a good dummy-proof guide on setting that up? That sounds exactly like why I bought the Pi in the first place

The easiest way is installing OpenWRT on the Pi

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