Penetration Testing-How to create a pen test lab

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PRACTICE MAKES PERFECT. CREATION OF A PENETRATION TESTING
LABORATORY, PROCEDURES AND TOOLS, START TO FINISH.
LQT2 Multimedia Presentation by Thomas Butler
Presented to the Information Technology College Faculty
of Western Governors University
in Partial Fulfillment of the Requirements for the Degree
Master of Science in Information Security and Assurance
February 26, 2013

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root@bt:~# WHOAMI?
Thomas Butler……Houston, Texas
CPA, CIA, CISA, CISSP, Security+, Network+, PMP
Over 20 years in DoD IT Audit (Retired)
Interested in IT Security & Penetration Testing
Started IT Security Consulting Co.-Dec 2011-http://www.butleritsec.com
Started WGU MS Degree-1 July 2012
WGU MS Degree Offers Credibility in IT Security

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PRESENTATION OVERVIEW-PER THE RUBRIC
Why I Chose This Project
Overview of Problem
What Project Consisted Of
Special Strategies Used
Successes In Achieving Milestones
Obstacles Encountered
What I Learned
How I Will Apply What I Learned

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WHY I CHOSE THIS PROJECT
A SERIOUS PROBLEM TO THE CYBERSECURITY OF THE NATION.
RESPONSE TO CURRENT CRITICISM THAT AVAILABLE SECURITY
CERTIFICATIONS DO NOT TEACH ENOUGH HANDS-ON PROCEDURES
AND THAT THEIR EXAMS DO NOT REQUIRE HANDS-ON BUT ARE
INSTEAD MULTIPLE CHOICE.
 DOD AND OTHER GOVERNMENT AGENCIES CLAIM EMPLOYEES
OBTAINING AVAILABLE CERTIFICATIONS CANNOT DO THE JOB REQUIRED
DUE TO LACK OF HANDS-ON SKILLS. TRAINING NEEDS TO EMPHASIZE
MORE HANDS-ON AND LESS BOOK KNOWLEDGE. (refer to news article in page 6)
 I COULD NOT FIND A TURN-KEY, OFF –THE-SHELF SOLUTION SO
I DECIDED TO CREATE ONE.
 I GOT ALL THE CERTS , THE CEH, CHFI, CISSP, SECURITY+, CCENT, BUT I NEED
HANDS-ON PRACTICE OR I WILL COMPLETELY FORGET EVERYTHING
I LEARNED.
 HANDS ON PRACTICE MAKES PERFECT AND INSTILLS CONFIDENCE.

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OVERVIEW OF PROBLEM DISCUSSED IN PROJECT
THE PROBLEM! Practice on systems you do not own without
written permission is illegal.
Need more hands-on.
I needed:
 A way to practice, ethically and legally
 All-in-one document
 Easy to follow. Easy to setup and use.
 Free and/or cheap
I could not find anything that satisfied all my needs, therefore, I decided to do
this project to create a practice lab for myself. Hopefully the project will benefit
others as well.

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CAUSES OF THE PROBLEM
High demand for penetration tests>government regulations & industry standards
a. PCI-DSS (Penetration Testing. Wikipedia, 2013) requires both annual and ongoing penetration testing
(after system changes).
a. FISMA -Federal Information Security Management Act (FISMA) via procedures promulgated by
NIST 800-53, Appendix E. (NIST 800-53, Rev. 3, 2009)
Shortage of well-trained penetration testers-THERE IS ARTICLE AFTER ARTICLE AFTER ARTICLE
a. A Barclay Simpson Corporate Governance Recruitment report on Information Security found that
the demand exceeds the supply of qualified penetration testers (Barclay Simpson, Corporate
Governance Recruitment, 2011).
b. US Air Force is planning on going on a “hiring binge” to hire 1,000 persons in cyber operations in
2014 (Magnuson, 1/17/2013). National Defense Industrial Association Magazine, 2111 Wilson Blvd.,
Suite 400, Arlington, VA 22201, Air Force Cyber-Operations Wing to Go on Hiring Binge).
c. Experts say DoD cyber workers undertrained By Zachary Fryer-Biggs - Staff writer
Posted : Saturday Feb 16, 2013 12:38:06 EST in the Federal Times a Gannett Pub.
http://www.marinecorpstimes.com/news/2013/02/dn-cyber-certification-
021613/?goback=.gde_54384_member_216288717
”Money is not being spent on hands-on training.” Others focused on the lack of hands-on training
required, resulting in broad certifications that are required for many jobs but are not specific
to any of them. Book training is simply not enough.”

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MORE CAUSES OF THE PROBLEM
Requires almost daily training reinforcement practice, or skills rapidly lost.
Every day new hacking software is introduced. Every day new vulnerabilities
are discovered.
How do you keep up if everything changes so rapidly?
Penetration testing is unique and very difficult because skills must be
transferred by computer keyboard>very labor intensive>requires humans to
think “outside the box”. No two infrastructures or system requires the same
penetration testing procedures.
How do you use what was learned in CEH when testing the client’s systems?

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STILL MORE CAUSES OF THE PROBLEM

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WHAT THE PROJECT CONSISTED OF
The project is documented in appendices A through G.
Appendix A: Creation of the Penetration Testing Lab
Appendix B: Penetration Testing Methodology
Appendix C: Reconnaissance and Information
Gathering
Appendix D: Active Scanning and Enumeration
Appendix E: Exploitation
Appendix F: Post-exploitation and Covering Tracks
Appendix G: Technology Terms/Acronyms

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WHAT THE PROJECT CONSISTED OF
Appendix A: Creation of the Penetration Testing Lab
Three virtual machines created within a Windows Vista OS using FREE
VMWare Player community edition
“Attack Machine” FREE Linux Ubuntu “Backtrack5R3”
”The pen testers premier OS and toolkit.”
“Victim Machine” FREE Linux “Metasploitable”-
OS-Created by Metasploit Project to allow hands-on practice
“Victim Machine” FREE Trinux “Badstore.net”-
vulnerable OS and Web App
Did I say FREE?

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WHAT THE PROJECT CONSISTED OF
Appendix B: Penetration Testing Methodologies
Penetration Testing Execution Standard, (2013) PTES. Retrieved 2013 from:
http://www.pentest-standard.org/index.php/Main_Page
Open System Security Testing Methodology Manual, (2013) ISECOM. Retrieved
2013 from: http://www.isecom.org/research/osstmm.html
Certified Ethical Hacker (CEH), (2013) Ethical Hacking. Retrieved 2013 from:
http://eccouncil.org
NIST 800-53, Appendix E. Retrieved from:
http://csrc.nist.gov/publications/PubsSPs.html#800-53

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WHAT THE PROJECT CONSISTED OF
Appendix C: Reconnaissance and Information Gathering
In summary of reconnaissance and foot printing, we have used the following for legal, passive,
reconnaissance and information gathering on J.C.Penney and have provided screen print proof
of concept (picture worth a thousand words). These tools are included in Backtrack5R3 or built
into command line.
Google-website URL, tons of other info;
Netcraft-OS & Web server running and IP address;
SmartWhoIs-Domain Registrar information
theHarvester-Emails and Sub-domains;
Maltego-Subdomains;
 traceroute/tracert command line-traces routers from origin to destination;
 nslookup command line-finds IP address from domain name>Linux “dig” and “host” are
alternatives, but NA in Windows

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WHAT THE PROJECT CONSISTED OF
Appendix D: Active Scanning and Enumeration
Using scanning tools in Backtrack5R3, we performed active scanning of
Metasploitable and Badstore.net, our “victims.” We provided screen
prints (picture worth a thousand words)for proof of concept. All these
tools are included in BT5R3.
 Nmap-port scan, OS version, services running;
 Nessus-port scans and vulnerability scans;
 Nikto (Wikto-Windows)-port scans and vulnerability scans;
 Metasploit-port, OS version, services running, vulnerability

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WHAT THE PROJECT CONSISTED OF
Appendix E: Exploitation with Metasploit
Metasploit-included free in Backtrack5R3-msfconsole. Proof of concept
screen prints (picture worth a thousand words) included in project.
Command line: root@bt:~# /pentest/exploits/framework2/msfconsole
OR>
root@bt:~# /opt/metasploit/msf3/msfconsole
modules: auxiliary, exploits, payloads
We also used Armitage-a GUI for Metasploit
Command line: root@bt:~# /opt/metasploit/msf3/armitage
modules: auxiliary, exploits, payloads

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WHAT THE PROJECT CONSISTED OF
Appendix F: Post-exploitation and Covering Tracks
Not a lot of in-depth information available on this topic!
Post-Exploitation: Got Root?, Elevation of privilege=Create
user, Add user to Admin Group; Offline and online password
attacks, John the Ripper, Pass the Hash, Cain and Abel.
Covering Tracks: Use Metaspoit to delete Event Logs. Use
Metasploit to remove file timestamps.

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WHAT THE PROJECT CONSISTED OF
Appendix G: Technology Terms/Acronyms
Includes 33 definition of terms

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SPECIAL STRATEGIES USED
Member of 41 Linked-In IT Security Groups>To share
information with IT security groups
Subscriptions to 35 IT Security Tutorial Blogs>To learn IT
security and ethical hacking
750 Linked-In Connections>To share information with IT
security individuals
Some basic knowledge of HTML, SQL, PYTHON

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SUCCESSES IN ACHIEVING MILESTONES
All files were downloaded and installed successfully with no problems
All three virtual machines were successfully created, opened
simultaneously, and run simultaneously on my Windows Vista box
with no memory problems. My Windows box has 4 G RAM and
I allocated 1G RAM for the “attack” machine and .5G RAM for each
“victim machine” leaving approx. 2 G RAM for the Windows box.
All penetration testing tools were run successfully and proof of concept
screen prints were obtained for all tools.

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OBSTACLES ENCOUNTERED
Limitation: Lab only includes software. Practice in this lab will not encounter
Hardware firewalls, routers, switches, hardware intrusion systems,
and other hardware security devices that would be encountered in a
real world penetration test.
I somewhat lacked an intermediate programming knowledge. I recommend
that the penetration testing student learn the following programming languages:
HTML to understand http requests and responses for use of
web proxies like Paros Proxy, Webscarab Proxy, Burp Proxy
SQL to understand SQL injection for use of tools like
SQLMap and manual injection of code
PYTHON to understand most of the penetration testing tools
in Backtrack5R3 for tools like theHarvester. The predominant
language for most tools in BT5R3 is python.
root@bt:~# ./theHarvester.py

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WHAT I LEARNED
A penetration test should not just be to gain access and get a shell and quit. It should be an audit of
the IT security posture and the goal should be to identify as many vulnerabilities as possible that need
fixing.
Money is wasted on training-Companies with a lot of money and the US Government (DoD) will send
their employees to SANS training for a 4 day crash course. Costs of travel, hotel, per diem, salary,
SANS Course fee could be > $10K for one student. Student returns to work and still cannot
do the job. (refer to recent news article in slide 6)
There has to be a better way. WGU is part of the solution to a better way
Cyberlaw, regulations, and compliance-Penetration testing without written permission is
illegal. Some regulations and industry standards require periodic penetration testing, i.e.
PCI-DSS, FISMA.
Leadership and professionalism-penetration testing is not a true profession like CPA, law,
medicine, etc. There is no barrier to entry. A barber needs a state license;
a penetration tester does not. Anyone can hold themselves out to be a penetration tester.
High ethical standards should be required for penetration testers.
Background checks, criminal checks, financial and credit checks, REFERENCES,
memberships in IT security organizations, and certifications.

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WHAT I LEARNED
Security Planning and Management- Organizations need to:
Start with a framework and set of internal controls such as ISO 27000/27001/27002;
Set a reasonable policy that can be followed and enforced;
Employee training ;
Create policy that requires vulnerability scans, periodic penetration testing,
periodic IT security audits, and periodic IT policy compliance audits.
Systems Security
No such thing as 100% security;
Penetration test is only one part of “defense in depth.” Perimeter defenses such as firewalls,
routers, switches, IDS/IPS, web application and database monitoring systems must be properly
configured;
 Patches and AV must be kept up to date.
Log files must be filtered (quantity reduced) and suspicious log entries must be examined.

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HOW I WILLAPPLY WHAT I LEARNED
I will apply the knowledge to running the company
http://www.butleritsec.com , an IT Security consultant
Company
I will apply the knowledge to provide best value to
clients in a highly ethical way.
I will continuously study and practice hands-on.
I am just beginning to learn.

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REFERENCES
Penetration Test, (2013) Wikipedia. Retrieved 2013 from: http://en.wikipedia.org/wiki/Penetration_test
NIST 800-53 and Federal Information Processing Standards (FIPS) 200 Retrieved from:
http://csrc.nist.gov/publications/PubsSPs.html#800-53.
Barclay Simpson, Corporate Governance Recruitment, (2011) Market Report on Information Security. Retrieved 2013
from: http://www.barclaysimpson.com/document_uploaded/BS_InfoSec_2011.pdf
Magnuson, (2013) National Defense Industrial Association Magazine, Air Force Cyber-Operations Wing to Go on
Hiring Binge. Retrieved 2013 from:
http://www.nationaldefensemagazine.org/blog/Lists/Posts/Post.aspx?ID=1026&goback=.gde_1836487_member_20563
4892
Penetration Testing Execution Standard, (2013) PTES. Retrieved 2013 from: http://www.pentest-
standard.org/index.php/Main_Page
Open System Security Testing Methodology Manual, (2013) ISECOM. Retrieved 2013 from:
http://www.isecom.org/research/osstmm.html
Certified Ethical Hacker (CEH), (2013) Ethical Hacking. Retrieved 2013 from: http://eccouncil.org
Experts say DoD cyber workers undertrained By Zachary Fryer-Biggs - Staff writer
Posted : Saturday Feb 16, 2013 12:38:06 EST in the Federal Times a Gannett Pub.
http://www.marinecorpstimes.com/news/2013/02/dn-cyber-certification-
021613/?goback=.gde_54384_member_216288717

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FINIS
A THANK YOU TO ALL THE WGU IT FACULTY
CINDY
WENDY
NORMA
CHARLES
AND MY MENTOR, BRETT
I HAVE THOROUGHLY ENJOYED THE EXPERIENCE
QUESTIONS FOR ME?