Tailscale Pihole Dns Routing

This skill should be used when a host or device on a network with both Tailscale and Pi-hole seems to bypass Pi-hole's ad-blocking despite DNS still resolving fine, when deciding whether to use Tailscale's tailnet-wide "Override DNS servers"/Global Nameservers setting (including whether to enable it for roaming ad-blocking), when a device's DNS silently breaks after that Override toggle is turned off, when Pi-hole silently rejects/resets DNS queries arriving over a Tailscale interface, or when systemd-resolved needs to be configured so a host gets Pi-hole for general DNS while keeping Tailscale MagicDNS working for *.ts.net hostnames. Trigger phrases include "tailscale override dns servers", "pihole bypassed tailscale", "resolv.conf generated by tailscale do not edit", "magicdns not resolving publicly", "systemd-resolved pihole tailscale", "Domains=~. resolved.conf", "tailscale accept-dns per device", "DNS=~. wildcard route", "pihole-dns-client playbook", "host missed by dns overhaul", "apt-get update failed after systemd-resolved install", "SSH_CLIENT tailscale IP over LAN hostname", "magicdns wrong answer right after tailscaled restart", "pihole listeningMode LOCAL", "dns.listeningMode ALL", "pihole rejects tailscale query connection reset", "roaming ad-blocking over tailscale", "nftables flush ruleset wipes tailscaled", "cloudflare backup nameserver tailscale unreliable", "tailscale global nameserver backup order", "ssh could not resolve hostname", "getent hosts not found but dig works", "ResolveUnicastSingleLabel", "single-label hostname resolution fails", "bare hostname ssh resolve failure ansible", "resolvectl query not found LLMNR", "restart of systemd-resolved failed exit status", "dns using direct mode directManager", "tailscale apt upgrade broke dns", "systemctl restart tailscaled did not fix dns", "resolv.conf plain file instead of symlink".

mkdir -p ~/.claude/skills/tailscale-pihole-dns-routing
curl -L https://claudskills.com/skills/tailscale-pihole-dns-routing/SKILL.md \
  -o ~/.claude/skills/tailscale-pihole-dns-routing/SKILL.md

@misc{tailscale-pihole-dns-routing-2026,
  author    = {jackson2w},
  title     = {Tailscale Pihole Dns Routing [Claude Code skill]},
  year      = {2026},
  publisher = {ClaudSkills},
  url       = {https://claudskills.com/skills/tailscale-pihole-dns-routing/}
}