[ericpauley]

Every TCP proxy (that doesn't thwart this) is detectable :)

Countermeasure: pick some min-RTT >= the actual client RTT (you can do this as a TCP proxy by measuring client ping). Measure server RTT and artificially delay responses to be >= min-RTT. This will require an added delay during the handshake and ACKs, but no added delay for the response payloads.

Counter-countermeasure: the above may lead to TCP message types that don't make sense given a traditional TCP client state machine (e.g., delayed ACK would bundle ACK and PUSH but the system shows separate/simultaneous ACK and PUSH packets. Counter-counter-countermeasure is left to the reader.

[Sakura-sx]

I think you could also compare with TLS handshake timings, delay for client hello among other things. And you could also compare it with HTTP RTT, not to mention that you can do TCP fingerprinting and compare it with the TLS and HTTP fingerprint of the browser, you can also measure the IP TTL and ping, among many other things... What I mean is that there are a ton of things that can be done on both sides, but any company with enough people working at this and enough servers will surely make something miles away from my proof of concept, and they also have a lot of traffic to know what's baseline data and what isn't.

It's a complex but fun world we live in hehe