Get some fundamental material about TCP/IP, ports and sockets, and
iptables too. . .
I don't know how you can cover penetration testing without
I'd give him a linux box and have him learn how to use openssh and
openssl fluently. Really, if he's interested in it, no text books
will make up for a good sandbox.
Hacking: the Art of Exploitation is an excellent book, I will say
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