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Pen Testing, Red Teaming, and More

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This is the slide deck that I used when presenting at FSU's Cyber Security Club. This presentation was supposed to give a description of what Red Teaming, Pen Testing, and other roles do.

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Pen Testing, Red Teaming, and More @ChrisTruncer
What’s this talk about? ● Who I am ● How I got started in the industry ● What is “red teaming” and/or “pen testing” ● Different Offensive Jobs ● Where is the field going? ● How to learn and get your foot in the door ● Questions
uid=0(@ChrisTruncer) ● Christopher Truncer (@ChrisTruncer) ○ Hacker ○ Open Source Software Developer ■ Veil Framework Developer ○ Florida State Seminole ○ Random certs… blah ● Red Teamer and Pen Tester for Mandiant
How I Started ● College ○ College computer security class ○ Hack my roommate ■ “Wow, hacking is real” ○ Took a security class ○ Decided this is what I wanted to do ■ …. is this even a job?
How I Started ● Start off in a technical role ○ Wanted to get a technical foundation before moving into security ● First job, not what I wanted ● Became a Sys Admin at Northrop Grumman ○ Stayed for about 2 years ● Began my plunge into security, and haven’t looked back
What is Penetration Testing or Red Teaming?
Different Job Descriptions ● Vulnerability Assessment/Assessor ● Penetration Tester ● Red Teamer ● Exploit Developer
Vulnerability Assessment/Assesso r
But that’s it… Kind of boring right?
Penetration Tester
Red Teaming is a little different, but similar
Red Teaming == Objective-Based Adversary Emulation
Pen Testing/Red Teaming Career Paths
Tale of Two Tracks ● All team members will typically start in a general pen testing position ● With experience, you will typically specialize ○ Red Team? Web Apps? Thick Clients? ● After specialization, two main tracks exist ○ Technical Track ○ Management Track
Tale of Two Tracks ● Technical ○ Performing research, or concentrating on leading technical challenges ■ Tech SME ○ Live and die by your own sword ● Management ○ Lead teams running assessments ○ Could stay technical… “It depends”
Tale of Two Tracks ● Both tracks have their pros and cons ● Honestly, just figure out what you love to do ○ It’s what the beginning stage of pen testing is designed to let you do ● Find your passion in this, and go for it ○ This field is filled by people who LOVE what they do
Exploit Developer
Exploit Developer ● Typically not on Ops ○ Not on keyboard ● Performing research on various technologies ○ Predominantly includes low-level analysis ■ Be very comfortable in a debugger and decompiler ■ Understand the basics of exploitation ● Buffer overflows, SEH overwrites, egghunters, etc.
Exploit Developer ● This can be really fun and rewarding ○ Perfect for people who really like taking apart puzzles and finding holes ○ Can be VERY time consuming - might take 6 months of research to find a vuln you can exploit ○ Might not find a vulnerability ○ Make a lot of money
Where is OffSec Going?
Where’s the field going ● Pen Testing and Red Teaming is relying less on technology, and more on people ○ Human error is easiest to exploits ■ Layoff Example ○ Misconfigurations/Poor configurations are what we look for now ■ User-Hunting ○ This is likely the way forward
Where’s the field going ● Exploitation is getting harder to do ○ Defensive technologies are making life hard ■ Used to see lots of exploits, post Win 7 -> not as much ○ Not many companies are offering pure exploit development positions ■ Government positions ■ Third party companies
Certifications ● They can be… ok.. ○ Sometimes needed to help get past HR ○ They are NOT a sign of competency ● Best certs, look at Offensive Security ○ OSCP - Pen Testing ○ OSCE - Exploit Development ● This style of certifications demonstrates knowledge and is respected
What I wish I knew ● Be prepared to be uncomfortable at times ○ Always in a new environment with new “stuff” and you’re expected to break it ○ Perk of the job too :) ● Build your process ○ Learn how you best approach networks, web apps, etc. ○ Use this to face what you don’t know
Get Into Coding ● Learning to code/script will be invaluable ○ Add functionality, or write your own tools ○ Manipulate large data sets ○ Nearly a requirement to be successful
Where to start coding? ● Pick a language to learn ○ Windows -> Powershell ○ Linux -> Bash, Python, or Ruby ● Find something tedious ○ Automate it!
How to Learn ● Go to security conferences! ○ Might be anywhere from $10 - $300 ○ BSides Conferences are local and almost always free, or super cheap ● Build your own lab ○ VMWare is your best friend ○ VulnHub ● Try free CTFs ● Twitter!
? Chris Truncer ○ @ChrisTruncer ○ CTruncer@christophertruncer.com ○ https://www.christophertruncer.com ○ https://github.com/ChrisTruncer

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Pen Testing, Red Teaming, and More

  • 1. Pen Testing, Red Teaming, and More @ChrisTruncer
  • 2. What’s this talk about? ● Who I am ● How I got started in the industry ● What is “red teaming” and/or “pen testing” ● Different Offensive Jobs ● Where is the field going? ● How to learn and get your foot in the door ● Questions
  • 3. uid=0(@ChrisTruncer) ● Christopher Truncer (@ChrisTruncer) ○ Hacker ○ Open Source Software Developer ■ Veil Framework Developer ○ Florida State Seminole ○ Random certs… blah ● Red Teamer and Pen Tester for Mandiant
  • 4. How I Started ● College ○ College computer security class ○ Hack my roommate ■ “Wow, hacking is real” ○ Took a security class ○ Decided this is what I wanted to do ■ …. is this even a job?
  • 5. How I Started ● Start off in a technical role ○ Wanted to get a technical foundation before moving into security ● First job, not what I wanted ● Became a Sys Admin at Northrop Grumman ○ Stayed for about 2 years ● Began my plunge into security, and haven’t looked back
  • 6. What is Penetration Testing or Red Teaming?
  • 7.
  • 8. Different Job Descriptions ● Vulnerability Assessment/Assessor ● Penetration Tester ● Red Teamer ● Exploit Developer
  • 10.
  • 11. But that’s it… Kind of boring right?
  • 13.
  • 14.
  • 15. Red Teaming is a little different, but similar
  • 16.
  • 17.
  • 20. Tale of Two Tracks ● All team members will typically start in a general pen testing position ● With experience, you will typically specialize ○ Red Team? Web Apps? Thick Clients? ● After specialization, two main tracks exist ○ Technical Track ○ Management Track
  • 21. Tale of Two Tracks ● Technical ○ Performing research, or concentrating on leading technical challenges ■ Tech SME ○ Live and die by your own sword ● Management ○ Lead teams running assessments ○ Could stay technical… “It depends”
  • 22. Tale of Two Tracks ● Both tracks have their pros and cons ● Honestly, just figure out what you love to do ○ It’s what the beginning stage of pen testing is designed to let you do ● Find your passion in this, and go for it ○ This field is filled by people who LOVE what they do
  • 24.
  • 25.
  • 26. Exploit Developer ● Typically not on Ops ○ Not on keyboard ● Performing research on various technologies ○ Predominantly includes low-level analysis ■ Be very comfortable in a debugger and decompiler ■ Understand the basics of exploitation ● Buffer overflows, SEH overwrites, egghunters, etc.
  • 27. Exploit Developer ● This can be really fun and rewarding ○ Perfect for people who really like taking apart puzzles and finding holes ○ Can be VERY time consuming - might take 6 months of research to find a vuln you can exploit ○ Might not find a vulnerability ○ Make a lot of money
  • 29. Where’s the field going ● Pen Testing and Red Teaming is relying less on technology, and more on people ○ Human error is easiest to exploits ■ Layoff Example ○ Misconfigurations/Poor configurations are what we look for now ■ User-Hunting ○ This is likely the way forward
  • 30. Where’s the field going ● Exploitation is getting harder to do ○ Defensive technologies are making life hard ■ Used to see lots of exploits, post Win 7 -> not as much ○ Not many companies are offering pure exploit development positions ■ Government positions ■ Third party companies
  • 31. Certifications ● They can be… ok.. ○ Sometimes needed to help get past HR ○ They are NOT a sign of competency ● Best certs, look at Offensive Security ○ OSCP - Pen Testing ○ OSCE - Exploit Development ● This style of certifications demonstrates knowledge and is respected
  • 32. What I wish I knew ● Be prepared to be uncomfortable at times ○ Always in a new environment with new “stuff” and you’re expected to break it ○ Perk of the job too :) ● Build your process ○ Learn how you best approach networks, web apps, etc. ○ Use this to face what you don’t know
  • 33. Get Into Coding ● Learning to code/script will be invaluable ○ Add functionality, or write your own tools ○ Manipulate large data sets ○ Nearly a requirement to be successful
  • 34. Where to start coding? ● Pick a language to learn ○ Windows -> Powershell ○ Linux -> Bash, Python, or Ruby ● Find something tedious ○ Automate it!
  • 35. How to Learn ● Go to security conferences! ○ Might be anywhere from $10 - $300 ○ BSides Conferences are local and almost always free, or super cheap ● Build your own lab ○ VMWare is your best friend ○ VulnHub ● Try free CTFs ● Twitter!
  • 36. ? Chris Truncer ○ @ChrisTruncer ○ CTruncer@christophertruncer.com ○ https://www.christophertruncer.com ○ https://github.com/ChrisTruncer

Notes de l'éditeur

  1. http://static2.techinsider.io/image/55ad5e1add0895810d8b45b5-2048-1365/6870002408_fb3bb8a069_k.jpg
  2. https://dilanwarnakulasooriya.files.wordpress.com/2012/07/52.png
  3. https://dilanwarnakulasooriya.files.wordpress.com/2012/07/52.png
  4. https://dilanwarnakulasooriya.files.wordpress.com/2012/07/52.png
  5. http://www.gannett-cdn.com/-mm-/0dafc0732cc7dc230df8135e882290d7c4c04efb/c=0-15-1325-1013&r=x404&c=534x401/local/-/media/USATODAY/GenericImages/2013/08/20/1377029409000-AP-Earns-UPS.jpg
  6. https://dilanwarnakulasooriya.files.wordpress.com/2012/07/52.png
  7. http://www.gannett-cdn.com/-mm-/0dafc0732cc7dc230df8135e882290d7c4c04efb/c=0-15-1325-1013&r=x404&c=534x401/local/-/media/USATODAY/GenericImages/2013/08/20/1377029409000-AP-Earns-UPS.jpg
  8. http://www.gannett-cdn.com/-mm-/0dafc0732cc7dc230df8135e882290d7c4c04efb/c=0-15-1325-1013&r=x404&c=534x401/local/-/media/USATODAY/GenericImages/2013/08/20/1377029409000-AP-Earns-UPS.jpg