Document everything. Found a useful link that helped you configure something? Copy the link. Finally got your proxy working right? Save the config. Even just make notes of how you set things up.
Refine and build you notes along with your knowledge.
Eventually, consider keeping all your config files in a self-hosted repository like Gitea.
Oh, and when stuff breaks it’s probably DNS.
A few things may be going on.
The errors seem focused on the tls certificate, which caddy tries to automatically provision.
First, in your caddyfile, “my.server” should reflect the real address used for access. Something like “jellyfin.my-domain.com”. This is important for the tls certificate to be generated correctly.
Once updated, pull out a cell phone, turn off wifi (use LTE/5G), and verify it can connect to your site. This makes sure you can access from outside your home network.
Once confirmed working, try again from your home network. Most likely the page will timeout. This will be due to DNS pointing you back to your own network, which can cause trouble. This can be solved several ways. One is by adding a static DNS entry which points to the IP of your caddy server. You can do this on a per system basis in the hosts file, or at the lan level with you DNS server or router, assuming it allows you to add a custom DNS entry. I do this with my Mikrotik router.
That should get things working internal and external.
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Firewatch is great! Since you liked that, also check out Life is Strange: True Colors
I see no reason you couldn’t. Just change the listen port on the nginx config to something other than 80 (so it doesn’t conflict), then tell treafik to send traffic to that port. Disclaimer, I’m not well versed with treafik, but have worked with several other reverse proxies to know the general idea.
I for one am happy to find a new self-hosted community starting here! It’s the one thing that kept me going back to reddit over the past few months but now am finding more and more I can shift my time here instead.
Per Caddy documentation, port 80 is also required, and now I suspect the not serving that port is causing Caddy to fail to issue you a tls certificate.
Try adding a simple text response like this (warning, formatting may not be perfect due to typing on mobile). Also setup a port forward on your router to your caddy host on port 80.
my-domain.com:80 { respond “Buzz off” }
Hopefully this will kick off the tls registration and then get your site on 443 working as well.