How to Setup A Pen Test Lab & How to Play CTF

By Anant Shrivastava http://anantshri.info

What is a Pen test Lab  A Pen testing Lab just like any other lab is a controlled environment where behavioral or operational patterns of a object / application could be studied for enhancement of skill / knowledge of the practitioner.  More specifically we try to create a replica of Wild Wild West and try to study it in a controlled manner Presentation by Anant Shrivastava for Null 2

Why  Give me six hours to chop down a tree and I will spend the first four sharpening the axe. -Abraham Lincoln  Practice enhances perfection  Do I need to say more….. Presentation by Anant Shrivastava for Null 3

What we will be practicing  A pentest lab could be a generalized lab or focused lab towards one single approach.  Such as  network testing  web app testing  malware analysis  mobile analysis  More and more… Presentation by Anant Shrivastava for Null 4

Standards good to know  OWASP – Open Web Application Security Project  OSSTMM - Open Source Security Testing Methodology Manual  ISO 27001 – auditing standard : (protection mechanism postmortem details). Presentation by Anant Shrivastava for Null 5

Lets Get Started  What are the basic requirements of a Pentest Lab.  Network  2-3 PC  Some vulnerable stuff.  Some toolset.  And of course a Twisted mind  Presentation by Anant Shrivastava for Null 6

Approach 1  Purchase a Switch/Router  Keep two powerful computers make one as target another as attacker.  PC target : could be loaded with prebuilt vulnerable software stacks. (examples ahead)  PC attack : load it with self build tool chain or prebuilt tool chain. Presentation by Anant Shrivastava for Null 7

Approach 2  Virtualization  1 Powerful Laptop / Desktop (>=4GB RAM, 64bit, 2.4+ preferable Quad Core)  Virtualization Solution  VMWare  Oracle Sun Innotek Virtual BOX   Microsoft virtual PC   Minimum 2 VM  Target  Attacker Presentation by Anant Shrivastava for Null 8

Attack Machine  Again Self Created or  Backtrack  Matriux  Moth/Lambert  Helix(Forensic Distro)  SIFT  Lots more google is your friend  I prefer Keeping a windows VM also and load tools specific to windows inside the VM Presentation by Anant Shrivastava for Null 9

Target Machine  Target Machine, either we can prepare ourself or use existing prebuilt images like  MetaSploitable  Unpatched Windows 2000, Xp  Damn Vulnerable Linux  de-ice  Hackerdemia  pWnOS  Ubuntu 7.04 Presentation by Anant Shrivastava for Null 10

Web Application testing  For Web applications You need some vulnerable Web application code  WebGoat  Hacme Tools(bank, Casion,Books,Travel…)  Damm vulnerable app  http://demo.testfire.net/  http://testasp.acunetix.com/  Or Download old version of joomla, wordpress, drupal set it up and you are good to go.. Presentation by Anant Shrivastava for Null 11

Do’s and Don’t  Avoid using main machine for any analysis.  Avoid Giving Read write access to VM over any folder of parent. (specially if VM and main OS are same)  Once your VM is prepared keep a screnshot. And you can use it as restore point after every session to get back to clean state. Presentation by Anant Shrivastava for Null 12

Network Testing  For Network Testing you could look at GNS3 for setting up the environment. (ciso/juniper routers / switches)  Would recommend : http://www.gns3.net/content/gns3-virtualbox-edition  Excellent guides are already available online  http://www.gns3.net/documentation Presentation by Anant Shrivastava for Null 13

Part 1 Over  However Does it satisfies your hunger?  Do you feel like conquering something even if you get inside one of the machine.  Initially yes but later NO.  It fails to satisfy the fun of manhandling the live target.  So lets see If we have any option of doing it within legal limits. Presentation by Anant Shrivastava for Null 14

Beyond just Lab 1. We can practice of online playgrounds. Live websites providing new challenges every now and then.  Honeynet.org 2. Hackthissite.org 3. Smashthestack.org 4. Intruded.net 5. intern0t 6. http://projectshellcode.com/ 7. For casual brain teasing Check hacker.org Are just a few examples 1. Presentation by Anant Shrivastava for Null 15

Beyond just lab  Practice on Live target’s willing to pay  Facebook.com  Mozilla for its products  Google.com Note : Do read the SOW and then only start. Presentation by Anant Shrivastava for Null 16

Capture The Flag  You can also participate in various CTF competition. (result fame and / or money besides increase in knowledge and confidence)  Capture the flag or CTF are competitions organized world wide in both online and offline mode.  People either team up and play against computer / organizer or are pitted against each other. Presentation by Anant Shrivastava for Null 17

Online CTF  When players play against organizer, they are given set of challenges which they need to complete within stipulated time limit and max scorer wins.  Some common characteristics  The challenges will try to touch all bases of ethical hacking (web app, RE, forensics, crypto and more)  You can keep your Zero days with you.  Generally challenges will be checking your approach and not how quickly you can skim through osvdb or exploitdb  Nearly 100% require documented approach to be a winner. Presentation by Anant Shrivastava for Null 18

Must have tools  These are tools and command that have made by must know how to use and must be ready to be used list Ping, ssh, telnet, scp, mount, fsck, file Nmap, gdb Strace, ltrace, ptrace Strings, Hexedit Wireshark, aircrack suite Firefox plugin set : tamper data, live header, firebug etc. Windows tools : Network Miner (this tool alone is my reason as of now to keep a windows VM)  Metasploit, burp/ZAP.        NOTE : YMMV : your mileage may vary Presentation by Anant Shrivastava for Null 19

One on One  This type of CTF is generally played in offline mode.  Each team is given a machine to play.  Machine contains a flag.  Task is to save your flag and also capture opponents flag.  This is Wild Wild West keep aside all books and start shooting as much arsenal as you have.  Good approach is to have few members focusing on hardening and others focusing on attack.  These events do see lots and lots of DDoS and DoS attacks Presentation by Anant Shrivastava for Null 20

Resources to follow  BackTrack Mailing list  Full Disclosure (select mailing list of interest)  Main full disclosure  Web application security  Security focus (select mailing list of interest)  Security basics  SANS Internet Storm Center  Darknet  To name a few Presentation by Anant Shrivastava for Null 21

Anant Shrivastava http://anantshri.info