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Then I found out my services would work better with Caddy
Exceptional idea. Cloudflare is nice, but Caddy will always win IMO. Additionally, considering you were able to get Caddy working, that simply drives home that unfortunately your reverse_proxy didn’t work because it was somehow misconfigured. Caddy is also a reverse_proxy.
My comment is pretty much what I said. You have an extremely complex environment that you’re not fully making use of. For example, you’re having issues with a reverse_proxy, but you had Tailscale presumably the whole time. Why not just use your VPN to reverse_proxy your requests if you were having issues?
Also using Caddy + Cloudflare is fine if you want to use cloudflare for DNS, however, Caddy handles all certificates itself. So you have Caddy, which can handle all the SSL certs itself, but you put Cloudflare on top of it to manage SSL certs. It’s just convoluted.
It’s a good environment, but a little overkill.
It’s pretty great. The only thing you have to remember is that the caddy instance and the container you’re proxifying have to be within the same docker network. So you’ll definitely want to use the caddy2 container if this is the setup you want to pursue.
If not then you can just use IP addresses inside or outside of a container it doesn’t matter.