Selfhosted
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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Can’t speak for OP but I was also attempting this and couldn’t get it working. My use case is that CF tunnels make multiple of my self hosted services available on the Internet via HTTPS and without directly exposing my home IP.
It does however mean that even when I use a service on my home network, everything is being proxied through CF which makes things much slower than they need to be 90% of the time. So my idea is to use caddy in parallel to CF and have a local DNS server point to my homelab, thereby circumventing the proxy whenever I’m on my home network.
But like I said I could not get this working just yet.
You'll need to disable proxy, run certbot, then re enable proxy.
LE won't sign a site already cf encrypted, or behind cf (even with cf SSL disabled.)
You could try a DNS challenge or other method.
https://letsencrypt.org/docs/challenge-types/