Hi all,
 First, you people have a great forum and the people are very friendly hats off to everyone and a very big Thank You for sharing knowledge

 Second, I am a system administrator for the past two years and of-late i am planning to move into security field(penetration testing) and become specialized in it.

 So with my limited knowledge I came upon this board and started reading all the threads and have come to a point where I am somewhat clear of what i need to do.

 I have passed RHCE and have a good understanding of Networking and *nix based systems but have very little knowledge of Windows with this background I plan to do the following to get me started in my path.

Step 1  Step 2   Step 3    Step 4      Step 5   Step 6      
RHCE      eCPPT   OSCP       M.S Security    Job          SANS Certs, CISSP
   
Things to know apart from RHCE in Step 1
----------------------------------------
01. Good basic knowledge of Networking (TCP - IP - UDP)
02. Basic to intermediate knowledge of Shell Scripting
03. Basic C and Python Programming

Things to know apart from eCPPT in Step 2
-----------------------------------------
01. Good understanding of *nix based OS
02. Internediate level to Advanced level knowledge in Networking
03. Good programming(Network releated) knowledge in C
04. Good understanding of ASM(x86,others) Programming
05. Good understanding of Windows OS

Things to know apart from OSCP in Step 3
----------------------------------------
01. Still have No idea, once I finish eCPPT I think I will know what to learn(just a guess tho)

Things to do in Step 4
----------------------
01. Get an internship in security firm to gain experience in the field
02. Prepare for OSCE

Things to do in Step 6
----------------------
01. After getting a job will do SANS Certification
02. After getting enough experience will do CISSP

Books I think which will help me
--------------------------------
01. Assembly Language Step-by-Step Programming with DOS and Linux by Jeff Duntemann
02. Build Your Own Security Lab - A Field Guide for Network Testing by Michael Gregg
03. Building Open Source Network Security Tools, Components and Techniques by Mike Schiffman
04. Counter Hack Reloaded by Edward Skoudis and Tom Liston
05. Crimeware - Understanding New Attacks & Defenses by Markus Jakobsson and Zulfikar Ramzan
06. File System Forensic Analysis by Brian Carrier
07. Google Hacking for Penetration Testers by Johnny Long
08. Hacking Exposed by Stuart McClure, Joel Scambray, and George Kurtz
09. Linux Firewalls: Attack Detection and Response with iptables, psad, and fwsnort by Michael Rash
10. Malware Forensics: Investigating and Analyzing Malicious Code - by Cameron H. Malin, Eoghan Casey, and James M. Aquilina
11. Network Intrusion Detection by Stephen Northcutt and Judy Novak
12. Practical Unix & Internet Security By Simson Garfinkel, Alan Schwartz, Gene Spafford
13. Rootkits: Subverting the Windows Kernel by Greg Hoglund and Jamie Butler
14. Security Metrics Replacing Fear, Uncertainty, and Doubt by Andrew Jaquith
15. TCP/IP Illustrated Volume 1 & TCP/IP Illustrated Volume 2 by Gary R. Wright and W. Richard Stevens
16. The Shellcoder's Handbook: Discovering and Exploiting Security Holes by Chris Anley, John Heasman, Felix Lindner, and Gerardo Richarte
17. The Tao Of Network Security Monitoring - Beyond Intrusion Detection by Richard Bejtlich
18. The Web Application Hacker's Handbook: Discovering and Exploiting Security Flaws by Dafydd Stuttard and Marcus Pinto
19. Virtual Honeypots -  From Botnet Tracking to Intrusion Detection by Niels Provos and Thorsten Holz
20. Linux Command Line and Shell Scripting Bible by Richard Blum

I subscribed to Bugtarq, Full disclosure, Pen Testing mailing lists.
I also subscribed to RISK newsletter from Qualys Inc, and reading every issue of Phrack to gain as much knowledge as possible.

 Sorry for making such a long post, but thought I will tell whatever I know and ask for guidance, can you please tell me of things I am missing, so i can learn and practice them?

thanks a lot for your time

dmef

Thanks sil,
 Regarding job, next August is when i can move from my current job position so I thought I better utilize the time in getting certifications, so only I pushed it to step 4.

 I need to do M.S due to some private constraints, so I thought I better do it in security which may help me during job hunting. And regarding certificates the path you have laid out is really wonderful, will plan around that.

 pentesting101 was really informative, will try to follow that schedule as much as possible apart form the certifications.

Thanks again for your kind and valuable feedback.

regards
dmef

In regards to language learning....depends what you know right now. Do you have any programming exp? I would say that scripting languages like python and perl are a thousand times easier than assembly and still easier than C but thats just me. As far as exploits go, you'll need to know a little of everything to get things to work right. I am by now means a good programmer but know how to read it and modify it.

I dont think that pentesting is just a flat set of skills. It's really an art form. There are multiple ways to nail a box, just depends how you want to do it and what you're better or worse at.

Thanks to the mods for sticky'ing this thread.  This is exactly what I was looking for!


I just read through the pentesting101 article you posted; lots of great information in there.  And I had never heard of the Wireshark cert before, so I went and read up on that also.  I had a question regarding the "alphabet soup" list.  You listed WCNA before CCDA studies.  Would doing networking studies before WCNA build a good foundation on understanding the WCNA material better?  I figured if Wireshark is used for troubleshooting network activity, etc, maybe it's better to do the network studies (which may or may not include obtaining a Cisco cert) prior to jumping into WCNA.  Thoughts?