Self-hosted Pi-hole and Tailscale setup fails silently after Tailscale's 180-day key expiry

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A developer running Pi-hole and Tailscale on a free Oracle Cloud VM in São Paulo lost DNS resolution across all devices after six months of smooth operation. The outage was traced to Tailscale's default 180-day node key expiry, which silently dropped the VM from the mesh network. Because the setup relied on a single DNS resolver — the now-unreachable VM — no fallback was available, blacking out name resolution on both a Windows 11 PC and a Galaxy S23 simultaneously. Internet connectivity itself remained intact, as confirmed by successful pings to public IPs, which helped isolate the failure to the DNS layer. The author has since documented the recovery process and flagged the key expiry behaviour as a critical detail for anyone running headless Tailscale nodes.

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