4 self-hosting failures that return success

The failures that cost me the most in three years of self-hosting were never the ones that threw an error. An error is a gift: it tells you where to look. The expensive ones are the failures that report success while being broken . A page that returns 200 OK . A healthcheck that says the container is fine. A backup that exits cleanly. A command that prints nothing wrong. Everything green, everything lying. Here are four of them, all from the same box (a 2016 desktop, i7-6700 / 32 GB, Docker behind Caddy, reachable only over Tailscale). Each fails by handing you a success signal. Each cost me an evening the first time. The fixes are boring once you know them, the point is knowing the failure exists. Sanitized skeleton with all the config at the end. 1. A loading page that returns 200 This one I could find nothing written about, so it cost me the most. To keep the box quiet, I run the heavy services on-demand: Sablier stops idle containers and starts them on the first request. Caddy (with the Sablier plugin) gates a virtual host behind a container group, serves a "please wait, starting up" page while the group boots, then proxies through: myhost . my - tailnet . ts . net : 8081 { route { sablier http :// sablier : 10000 { group office session_duration 30 m } reverse_proxy nextcloud : 80 } } I gate my whole Nextcloud vhost, WebDAV included, this way. And here is the silent failure: if the gated group is not healthy, Sablier serves that HTML loading page for every request, and it serves it with 200 OK . A browser shows a spinner, fine. But my Obsidian vault syncs over WebDAV, and a WebDAV client asking for a directory listing got a 200 with a chunk of HTML instead of the XML it expected. Sync died with a cryptic no root multistatus found . Nextcloud itself was up and perfectly healthy the whole time. Every uptime check I had was green, because the gate in front kept answering 200 . The structural lesson: the moment you put a service on-demand behind a reverse proxy, tha