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.

  • chiisana@lemmy.chiisana.netEnglish
    9·
    2 months 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.

  • just_another_person@lemmy.worldEnglish
    8·
    2 months ago

    Having an HTTPS enabled server behind a proxy means the server is connecting with the proxy endpoint. That’s not how HTTPS works. If you want HTTPS enabled for a server BEHIND a proxy, you would do it at the original hand off (forward proxy), in this case meaning the Cloudflare proxy that clients connect to.

    You’re seeing the errors because the proxy backend is being told to speak HTTPS with Caddy, and it doesn’t work like that.

  • Max-P@lemmy.max-p.meEnglish
    6·
    2 months ago

    If you’re behind Cloudflare, don’t. Just get an origin certificate from CF, it’s a cert that CF trust between itself and your server. By using Cloudflare you’re making Cloudflare responsible for your cert.

  • Cyberflunk@lemmy.worldEnglish
    2·
    2 months ago

    In this episode of “Doing everything the hardest way possible.”

    Cloudflare has SSL, y u need mo?

    • Akinzekeel@lemmy.worldEnglish
      1·
      2 months ago

      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.

      • mik@sh.itjust.worksEnglish
        1·
        2 months ago

        I run the setup you’re aiming for, and as the other guy said, DNS challenge is the way to go. That’s what I do, and it works beautifully. It even works with Caddy auto-https, you just need to build Caddy with the cloudflare-dns plugin.

  • Decronym@lemmy.decronym.xyzBEnglish
    1·
    2 months ago

    Acronyms, initialisms, abbreviations, contractions, and other phrases which expand to something larger, that I’ve seen in this thread:

    Fewer Letters More Letters
    CF CloudFlare
    DNS Domain Name Service/System
    HTTP Hypertext Transfer Protocol, the Web
    HTTPS HTTP over SSL
    IP Internet Protocol
    SSL Secure Sockets Layer, for transparent encryption

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