I would advise you to remove the rule on your router and expose your services with cloudflared instead. It should get you started with securely hosting your websites. Then you can build up on this self-hosting knowledge and later decide if you want to manage this yourself.
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When you tried caddy and received an error, that looks like you are getting the wrong image name.
Then you mentioned deleting caddyfile as the configuration didn’t work. But, if I am following correctly the caddyfile wouldn’t yet be relevant if the caddy container hadn’t actually ran.
Pulling from Caddys docs, you should just need to run
$ docker run -d -p 80:80 \
-v $PWD/Caddyfile:/etc/caddy/Caddyfile \
-v caddy_data:/data \
caddy
Where $PWD is the current directory the terminal is currently in.
Further docs for then configuring for HTTPs you can find here under
Automatic TLS with the Caddy image
I have not tried caddy through docker yet, just running it through a windows command line with admin priv. I'm looking into doing it with Docker, just haven't started yet.
I will remember how familiar you are with docker!
I'm not super familiar with docker so im sorry im not much help there but i noticed that you mentioned a ATnT router. Are you using them as an Internet provider?
If so, you might have a carrier grade nat which makes reverse proxy like this not possible even if you do get caddy server working. I had a similar situation with my jellyfin server.
I had caddy server working but when i moved and started using a mobile internet provider, i had to use a vpn tunnel like cloudflare or zerotier to get around it.
All this to say, id recommend finding that out so if that is the case you dont spend anymore time on caddy.
Good luck either way.
I'm betting you've nailed it. It doesn't make sense to me why it won't work. You're also the second one to mention cloudflared. It is easy to set up?
ATnT should be able to tell you for sure. I remember reading about another person facing a cgnat using ATnT on reddit while i still went there so it very well could be.
And fairly easy setup yea. I did mine using a windows pc for testing as i was kinda in between places at the time and thats what i ended up using for jellyfin as well. Just lives on my media pc at the moment. The docs are pretty straight forward.
I recommend that or zero tier which is even more dead simple. Both are good but cloudflare does care about how much bandwidth you're using so just bear that in mind if you think you'll use the server for anything else.
Both are vpn tunnels so either should work just fine.
https://developers.cloudflare.com/cloudflare-one/connections/connect-networks/
https://www.zerotier.com/pricing/
Self hosting can get pretty overwhelming but i find that using docs in addition to youtube videos helps a lot. I also recommend giving Linux a go when you feel up to it. It can be a very nice option if you're working with older hardware.
I've been messing with Linux on and off since 2005. Anything beyond normie operations usually ends in frustration.
Oh I'm not calling those bastards at ATT- fuggin hate 'em
Use Tailscale with the Funnel option.
It provides a fully encrypted connection for external devices that don't have the Tailscale client. Pretty impressive.
Similar to using Cloudflare tunnels but easier to setup.