this post was submitted on 17 Sep 2024
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I cannot seem to figure out how to get caddy automatic HTTPS to work behind cloud flair proxy. (lemmy.world)
submitted 1 month ago* (last edited 1 month ago) by douglasg14b@lemmy.world to c/selfhosted@lemmy.world
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Hopefully you all can help!

I've been to hundreds of threads over the last few days trying to puzzle this out, with no luck.

The problem:

  1. Caddy v2 with acme HTTP-1 ACME challenge (Changed from TLS-ALPN challenge)
  2. Cloudflair DNS with proxy ON
  3. All cloudflair https is off
  4. This is a .co domain

Any attempt to get certificates fails with an invalid challenge response. If I try and navigate (or curl) to the challenge directly I always get SSL validation errors as if all the requests are trying to upgrade to HTTPS.

I'm kind of at my wit's end here and am running out of things to try.

If I turn Cloud flare proxy off and go back to TLS-ALPN challenge, everything works as expected. However I do not wish to expose myself directly and want to use the proxy.

What should I be doing?

I have now solved this by using Cloudflair DNS ACME challenge. Cloudflair SSL turned back on. Everything works as expected now, I can have external clients terminate SSL at cloudflair, cloudflair communicate with my proxy through HTTPS, and have internal clients terminate SSL at caddy.

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[–] chiisana@lemmy.chiisana.net 9 points 1 month ago

It is easier to think of the SSL termination in legs.

  1. Client to Cloudflare; if you’re behind orange cloud, you get this for free, don’t turn orange cloud off unless you want to have direct exposure.
  2. Cloudflare to your sever; use their origin cert, this is easiest and secure. You can even get one made specific so your subdomains, or wildcard of your subdomain. Unless you have specific compliance needs, you shouldn’t need to turn this off, and you don’t need to roll your own cert.
  3. Your reverse proxy to your apps; honestly, it’s already on your machine, you can do self signed cert if it really bothers you, but at the end of the day, probably not worth the hassle.

If, however, you want to directly expose your service without orange cloud (running a game server on the same subdomain for example), then you’d disable the orange cloud and do Let’s Encrypt or deploy your own certificate on your reverse proxy.