I have a home server and I have some HTTP services running on it. I’m thinking if I should even bother with HTTPS, as I’m already using tail scale which should be peer-to-peer and encrypted. So I shouldn’t worry about any men in the middle.

Am I missing something?

It just feels wrong to work with non-S HTTP :(

I might have misunderstood you, but data transferred inside the tailnet will always be encrypted by Tailscale.
So if you’re connected to a public wifi and someone’s looking at your traffic, accessing a random http site would be clear text, but accessing an http site inside your tailnet will be encrypted.

Unless you define an exit node and tell Tailscale to use it. And then all your traffic will be encrypted from the view of the one looking at your traffic logs from the public wifi (and clear text from the exit node to the random http site).

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Yes, I misread and immediately deleted my post lol. I think you were talking about tailscale VPN, and I was thinking something more like cloudflare tunnel.

That said, the risk is still there that tailscale (or whichever middle company) can read your plaintext packets.

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