Bootcamp #15: Digital War Games

Reading List:
The Tangled Web
Shell Coding
Past Def-Con CTF Writeups

Video Supplement:
Assembly language megaprimer for Linux and Windows
Collaborative Pentesting with Lair
Automated Wordlist Generation

Hands On:
Run through Web For Pentester II
Check out the war games at Smashing The Stack
Check out the war games at Over The Wire

Check out these Android Pentesting VMs!

Programming:
Awesome Programming Exercises and Competitions
The Corelan Exploit Writing Tutorials

Bonus War Games:
CapTF repository of old CTF challenges.
Shell-Storm repository of old CTF challenges.
WeChall ranked hacking challenges.