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This question has been asked before a number of times, but I seek a more in-depth answer: The objective is to mitigate the risk of being identified, by setting up chained VPN services so that the VPN on the second layer does not know my real IP address, and the VPN on the first layer does not know what I am accessing (even if the services' operators choose to look at or keep track of such identifying information). Two solutions I've come across have caught my attention. Other solutions are too unfeasible to setup due to costs and procedures involved.

Leaving aside the concept of money trails (that can be feasibly mitigated by a number of practices), here is what got me interested:

  • Connect Computer A to a VPN service, and from that, remotely connect to a Computer B. Then connect Computer B to a different VPN service, and finally use that to access the intended target.

  • Create a Virtual Machine with a NAT adapter. Use a VPN service A on the host machine. Boot up Virtual Machine B and connect to another VPN service B there.

Does this actually mean my data is going through both VPNs? Is there a failsafe procedure that I could utilize to verify the existence of both layers? Will the VPN on the second layer receive only encrypted data instead of only plain text (as would happen normally, with a trivial one VPN setup)?

Furthermore, which software would you recommend in order to prevent leaks in case one VPN goes offline for some reason (cut all network traffic immediately once VPN is offline)?

Thanks!

marked as duplicate by WhiteWinterWolf, Neil Smithline, Xander, Rory Alsop Dec 30 '15 at 11:03

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