[Network] Reaching the right target

[Miguel Regala <mikfisher64 () gmail com>]

Dear list,

One thing that confuses me is doing a pentest of a machine across the
wan, using a VPN or a proxy chains. The thing is, how do i know that i
have a reliable, virtual pipe? i.e there are times when i can ping a
webserver and i reach the intended target and others i am
pinging/scanning some middle device.

Bottom line:
a) How can I be sure I'm reaching the right target and have a reliable
connection between my machine and the target? (without loss of
packets, etc)
b) is there anyway i can assess the problem? That is discover what's
preventing me for reaching the target.

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