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varsock ,

hmm, I’m not sure I agree - or perhaps I didn’t explain myself well previously and caused confusion between us.

Yes I agree with you in your description of how cloudflare encrypts -> decrypts -> encrypts; they are allowing you to ride over their network. If you remove cloudflare from the picture entirely, then you just have the internet facing server.

What I’m saying is, if the client and endpoint (server) talk in an encrypted protocol, then cloudflare cannot MiTM the data, only the IP headers. This is similar if you were to connect to any ol’ website over an ISP’s network. If your session is not HTTPS, then your application data can be read. You can have encrypted sessions inside of CF tunnel-network-tunnel.

If your services support encryption, great. But you can also expose a wireguard endpoint so you have the following

wg client --(tunnel to CF)–> CF network --(tunnel to your server)–> wireguard server

the real advantage to CF tunnel is hiding your IP from the public internet, not poking any holes in your firewall for ingress traffic, and cloudflare can apply firewall rules to those clients trying to reach your server by DNS hostname.

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