TLS Handshake timeouts with an EOF in logs

[Pixiestix (Leon)]

Thank you for that, it seems that helped make sense of the second response. I am trying to migrate to Caddy from an old gateway service I was using. It used to handle my certificates and my reverse proxy.

What I did was, I transferred the domains to another DNS provider and want to use caddy to manage the certificates and reverse proxy from them now.

The idea was my home router forwards all port 80 and 443 to Caddy lxc container, and than any non-80 or 443 would go through the old gateway instead. The reason is the old gateway has fail2ban and other stuff I had setup for protection, but it’s dynamic DNS system does not support my new DNS provider, but Caddy does.

I tried to hack my network around to follow this diagram more-or-less

Using Caddy as a reverse proxy in a home network

If you want to run a service inside a Local Area Network (LAN) such as your home or office – and especially if you want to be able to access it from outside that network – Caddy can help you accomplish this quite easily. This guide will show you how. It assumes you’ve never done this before, but that you have some technical proficiency and are somewhat knowledgable about your own network. Do this at your own risk. There are several ways to make private services accessible from other n…

So before it was Home router → Old gateway server

Now what I’m trying to do is Home router → Http(s) to Caddy else → to old gateway

I noticed that the 2nd response resulted from the caddy lxc pointing to the old gateway as it’s DNS. When I switched the DNS to my home router , it now has the same hanging issue as the first output.

Am I just placing caddy in the wrong part of my network? I figured i could it between my home router and my old gateway.

Hopefully this made sense.