this post was submitted on 05 Feb 2025
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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.