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Can one observe the IP address of his entry node with "tracert"? In fact, what type of information does "tracert" is able to observe on Tor network?

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Tor is only used for tunneling TCP packets. By default traceroute sends UDP or ICMP (Internet Control Message Protocol) packets, ergo it can't be routed through Tor.

However, it's also possible to send TCP SYN's to do essentially the same thing. If you used traceroute to print a series of SYN-ACK's, you would see the path from the exit node to the final destination (as if you'd run the traceroute from the exit node).

(For clarification, tracert is a Windows only utility; every other operating system calls it traceroute. I have no idea if the Windows version behaves the same way as normal traceroute.)

If all you want to do is find the IP address of your entry node, you can simply ask Tor for information about the current streams. There should be several questions on here about how to do that, or you can use a UI such as Arm.

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