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You're thinking of these as Single Points of Failure, but they're not in parallel; they're in series.

Consider the attacker: a service you've visited that has your "outermost visible" IP, and wants to know who you are. From their perspective, it doesn't matter if your ISP is willing to give information freely, because they don't know who your ISP is until they've already gotten the information from your VPN provider. Each layer prevents the layer below it from being attacked, until it is removed.

Yes, a state actor could just ask "every ISP at once" to look at their logs of OpenVPN-protocol traffic and identify the packets that match the ones that arrived at the service. But state actors aren't the usual attacker profile, and require entirely different strategies (e.g. getting human "proxies" to use Internet cafes for you.)



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