AnonymousDeity,

{“level”:“error”,“ts”:1691499478.2793655,“logger”:“tls.handshake”,“msg”:“getting certificate from external certificate manager”,“remote_ip”:“100

.125.48.40”,“remote_port”:“60140”,“sni”:“machine.domain.ts.net”,“cert_manager”:0,“error”:“Get "local-tailscaled.sock/localapi/v0/…/vaulty.tail

a5148.ts.net?type=pair": dial unix /var/run/tailscale/tailscaled.sock: connect: no such file or directory”}

This is your main issue - looks like Caddy can’t access the tailscale socket in order to serve their TLS cert. check you’re running caddy>2.5, check the socket exists and check the user running the caddy process has access to it. docs

Are you running Caddy with docker?

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