Caddy v2.11.4's caddyfile adapter rejects 'tls { insecure_skip_verify }'
inside transport http (unrecognized subdirective '{') and also rejects
the handler-level form. The working form, verified live against PMS with
a throwaway caddy (200 OK), is the bare token:
reverse_proxy 192.168.0.235:32400 {
transport http {
tls_insecure_skip_verify
}
}
PMS 1.43.x on :32400 accepts, reads, and silently closes every non-TLS
connection from a non-loopback source (loopback exempt). The plain-HTTP
reverse_proxy therefore got EOF and Caddy answered an empty-body 502.
Both Plex vhosts now dial the upstream over TLS with
insecure_skip_verify (PMS self-signed cert, pinned LAN hop only;
client-facing Let's Encrypt TLS unchanged).
The Caddyfile had 'admin off', which disables Caddy's config file
watcher. Rendered Caddyfile changes never loaded until the container
was recreated, so the double-hash basicauth fix sat on disk unapplied
across deploys (2026-08-22). Admin binds to 127.0.0.1:2019 inside the
container and the port is unpublished, so nothing outside reaches it.
deploy.sh now issues an explicit 'caddy reload' (retry loop) after
'up -d', with the file watcher as backstop.
basicauth (2026-08-22 incident):
- the Caddyfile template carried its own $2a$14$ prefix and deploy.sh
substituted the full hash (prefix included), rendering an invalid
double-prefixed hash. Every basicauth vhost rejected every password
with 401 and Caddy logged nothing.
- template is now a bare REPLACE_WITH_HASH token; tests pin the render
contract (no prefix in template; rendered line is exactly 'dank <hash>').
open-webui (2026-08-22 incident):
- its slirp4netns helper process died, leaving the container running
with only 'lo' in its netns: port 3005 accepted TCP and reset every
request, so chat served empty responses for ~2 days, unlogged.
- move to a pinned bridge network (systemd-open-webui, 10.89.3.0/24,
gw 10.89.3.1) — no per-container helper to die.
- LLM endpoint reached via the gateway (host.containers.internal is
slirp-only): OPENAI_API_BASE_URL=http://10.89.3.1:52625.
- add a quadlet healthcheck: /health (app) + non-loopback interface
(network liveness; the dead-tap state leaves only 'lo').
- deploy script now copies the .network file too.
- docs updated (OpenWebUI History section, Caddy basic-auth contract).
Frank