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I don't get why he says "VPN connection to TOR => GOTOJAIL".

How is it OK that your ISP sees you connecting to Tor, but dangerous if your VPN provider does? Or is this about some other issue?

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Yes, hard to understand why he says that, maybe he meant TOR connection to VPN?

He says that Tor to VPN is OK, as long as you buy the VPN service anonymously. So I don't think that there's semantic confusion. Also, there is a clear downside to tunneling VPNs through Tor, in that it prevents circuit switching, which increases vulnerability to deanonymization.

The NSA sees all. Using both a VPN and Tor is more suspicious than just using Tor.

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