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> > Are there ways to do trace routes to particular ports? > No. Your best bet here is to use a packet sniffer at various points of the process. > if I have him do it from windows (dos), would it be the > same as from his browser? As far as NAT and routing, yes. They use the same TCP/IP stack. However, sometimes there are proxies configured for the web browser to use that won't be used automatically by other apps. (Theoretically, you could write apps that read it's settings so that you could use them yourself, but I don't know of many -- other than Microsoft apps -- that do this.)
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