Last time, we talked about setting up Caddy as a reverse-proxy to puma-dev, providing automatically-managed local development Rails apps on their own dedicated .test domains. Either I missed this back then, or something inside puma-dev or Caddy changed in the meantime, but SSL requests stopped working inside Rails apps today, and it took me a while to figure out what was happening.

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Caddy plus puma-dev with SSL 23 Jul 2023. SSL requests stopped working inside Rails apps today, and it took me a while to figure out what was happening. With this slightly more complicated Caddy config block, SSL is again working.