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When is a Red Team a Red Team?
M AY 2 0 1 9
Agenda
[+] Introductions 1m
[+] Setting the Stage 5m
[+] Tales from the Trenches 13m
[+] Conclusion 1m
> whoami
• Sanjiv Kawa
• Penetration Tester and Red Teamer
• I Lead Nettitude's Penetration Testing Team
kawabungah
skahwah
> whois Nettitude
• 160 security professionals
• Global presence
• Significant Industry Influence
Nettitude’s Research and Zero Days
Setting the Stage
Confusion
• What is Red Teaming?
• Who is it for?
• What does it achieve?
• Why is it important?
The Current State of Technical Assurance
The Current State of Technical Assurance
What is a Red Team Engagement?
PenTest+
Purpose of a Red Team Engagement
Holistically test your organization against a real world breach scenario
Driven from real world threats Focus on Depth and not Breadth Exercise your Blue Team
People Process
Technology
https://www.flaticon.com/free-icon/team_476700
https://www.flaticon.com/free-icon/settings_126472
https://www.flaticon.com/free-icon/laptop_114734
What Does a Red Team Engagement Look Like?
What Does a Red Team Engagement Look Like?
What Does a Red Team Engagement Look Like?
Why is Red Teaming Important?
Exercise Your Blue Team
People Process
Technology
Tales from the Trenches
Some of our Achievements
• We get to work with some awesome clients
• We have an extremely high success rate in reaching objectives
Some of our Achievements
• We get to work with some awesome clients
• We have an extremely high success rate in reaching objectives
https://www.flaticon.com/free-icon/bank_1066122
https://www.flaticon.com/free-icon/medical-history_1685819
https://www.flaticon.com/free-icon/benefits_1369921
https://www.flaticon.com/free-icon/family_1396773
Tales from the Trenches
I’m going to walk you through a red team engagement we did for a
stock exchange
Tales from the Trenches
Disclaimer:
Some areas have been replaced with fictitious people, other areas
are heavily redacted to protect the identity of the Client and their
employees …
Engagement Particulars
Client: Large Stock Exchange
Objective: Integrity of Real Time Trading System (TS)
Assessment: Threat Intelligence
Scenario 1: External Threat
Scenario 2: Insider Threat
Assessment: Detection and Response Capabilities
Threat Intelligence
Mitre ATT&CK Group ID:
G0032
AKA: Lazarus Group
North Korea
Threat Intelligence: Lazarus Group
Based on TI: Initial entry is going to be a targeted phish
Threat Intelligence: Recon
If I had 8 hours to chop down a tree, I would spend 6 of those
hours sharpening my axe
Many, many, many tools ...
Threat Intelligence: Finding Targets to Phish
• In-house developed,
publicly available tool
• Checks HIBP for breaches
• Name, email, title, etc
Threat Intelligence: Building Pretext
• Find target employees who work with TS
• Senior Trader at Stock Company
• Works with TS
• A+ candidate to phish!
Threat Intelligence: Building Pretext
Threat Intelligence: Building Pretext
Priority Target at Stock
Exchange
Position Pretext from LinkedIn
1 Rey Oakley Senior Trader Joseph Thompson – Capital Ventures
2 Mike Cortes IT Support Sarah Cho – Computer Stop
3 Karen Hayes Database Admin John Smith – DevShop
4 Stacy Chan Project Manager Mike Jacklin – Logistics R Us
• Don’t stop at one, maximize your chances.
Handover
At this point, the TI Team hands over a “target pack” to the Red Team
External Threat: Delivery
External Threat: Delivery
External Threat: Weaponization
External Threat: Delivery and Execution
• Pretext: Recruitment and Career Opportunities
• Delivery: Targeted Phishing (4 users)
• Objective: Impact the Integrity of TS
0
1
2
3
4
5
Users Targeted Emails Confirmed Opened Links Clicked Command and Control Obtained
Targeted Phishing Statistics
External Threat: Execution
Execution? Target at Stock
Exchange
Position Pretext from LinkedIn
ý Rey Oakley Senior Trader Joseph Thompson – Capital Ventures
ý Mike Cortes IT Support Sarah Cho – Computer Stop
þ Karen Hayes Database Admin John Smith – DevShop
þ Stacy Chan Project Manager Mike Jacklin – Logistics R Us
• Who’s workstation are we on?
External Threat: Acting on Objectives
Karen Hayes
External Threat: Acting on Objectives
þ Know where TS Lives
þ Know users who access TS
Karen Hayes
Global File Share TS Documents
Active Directory TS Users
External Threat: Acting on Objectives
Compromised
Workstation
Trader
Workstation
External Threat: Acting on Objectives
Karen Hayes
Karen Hayes
Active Directory
External Threat: Acting on Objectives
Karen Hayes
Karen Hayes
Citrix User
CVE-2018-6857: Sophos Safeguard Priv Esc 0-day
External Threat: Acting on Objectives
Karen Hayes
Citrix Administrator
Workstation Administrator
Other Citrix Servers
External Threat: Acting on Objectives
Compromised
Workstation
Trader
Workstation
External Threat: Acting on Objectives
Compromised
Workstation
Trader
Workstation
Workstation
Administrator
External Threat: Acting on Objectives
Trader Workstation
Now What?
Detection and Response Assessment
Detection and Response Assessment Outcomes
Blue Team had many chances to see what we did. What did they
actually see?
1. Ascertain timeline of detected events
Detection and Response Assessment Outcomes
Blue Team had many chances to see what we did. What did they
actually see?
1. Ascertain timeline of detected events
2. How repeatable was the detection method and response?
3. Formal reporting to stakeholders
4. Tools and techniques used in response
5. Lessons learned
Detection and Response Assessment Outcomes
1. Attempt to identify weaknesses in people, processes and
most importantly technology which is constraining the
detection process
2. Identify areas of strength and significant capability
3. Work together to implement and test these changes
Conclusion
Conclusion
• Test people processes and technology
• Test Blue Teams ability to respond to a threat
• Not a replacement for penetration testing
• Assurance activities should be continuous
• Improve security posture
Thank You
INTENTIONALLY BLANK
TITLE
Insert content
Insert Content
• Insert Content
Purpose of a Red Team Engagement
Holistically test your organisation against a real world breach scenario
Strong / Weak
Security Posture
PROCESS
PEOPLE
TECHNOLOGY
56
• Measure IR/EDR Capability (Blue Team)
• Focus on Depth and not Breadth
• Driven from Real World Threats
External Threat: Acting on Objectives
Why is Red Teaming Important?
A few examples where People, Process, and Technology fell down…
58

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When is a Red Team a Red Team

  • 1. When is a Red Team a Red Team? M AY 2 0 1 9
  • 2. Agenda [+] Introductions 1m [+] Setting the Stage 5m [+] Tales from the Trenches 13m [+] Conclusion 1m
  • 3. > whoami • Sanjiv Kawa • Penetration Tester and Red Teamer • I Lead Nettitude's Penetration Testing Team kawabungah skahwah
  • 4. > whois Nettitude • 160 security professionals • Global presence • Significant Industry Influence
  • 7. Confusion • What is Red Teaming? • Who is it for? • What does it achieve? • Why is it important?
  • 8. The Current State of Technical Assurance
  • 9. The Current State of Technical Assurance
  • 10. What is a Red Team Engagement? PenTest+
  • 11. Purpose of a Red Team Engagement Holistically test your organization against a real world breach scenario Driven from real world threats Focus on Depth and not Breadth Exercise your Blue Team People Process Technology https://www.flaticon.com/free-icon/team_476700 https://www.flaticon.com/free-icon/settings_126472 https://www.flaticon.com/free-icon/laptop_114734
  • 12. What Does a Red Team Engagement Look Like?
  • 13. What Does a Red Team Engagement Look Like?
  • 14. What Does a Red Team Engagement Look Like?
  • 15. Why is Red Teaming Important? Exercise Your Blue Team People Process Technology
  • 16. Tales from the Trenches
  • 17. Some of our Achievements • We get to work with some awesome clients • We have an extremely high success rate in reaching objectives
  • 18. Some of our Achievements • We get to work with some awesome clients • We have an extremely high success rate in reaching objectives https://www.flaticon.com/free-icon/bank_1066122 https://www.flaticon.com/free-icon/medical-history_1685819 https://www.flaticon.com/free-icon/benefits_1369921 https://www.flaticon.com/free-icon/family_1396773
  • 19. Tales from the Trenches I’m going to walk you through a red team engagement we did for a stock exchange
  • 20. Tales from the Trenches Disclaimer: Some areas have been replaced with fictitious people, other areas are heavily redacted to protect the identity of the Client and their employees …
  • 21. Engagement Particulars Client: Large Stock Exchange Objective: Integrity of Real Time Trading System (TS) Assessment: Threat Intelligence Scenario 1: External Threat Scenario 2: Insider Threat Assessment: Detection and Response Capabilities
  • 22. Threat Intelligence Mitre ATT&CK Group ID: G0032 AKA: Lazarus Group North Korea
  • 23. Threat Intelligence: Lazarus Group Based on TI: Initial entry is going to be a targeted phish
  • 24. Threat Intelligence: Recon If I had 8 hours to chop down a tree, I would spend 6 of those hours sharpening my axe Many, many, many tools ...
  • 25. Threat Intelligence: Finding Targets to Phish • In-house developed, publicly available tool • Checks HIBP for breaches • Name, email, title, etc
  • 26. Threat Intelligence: Building Pretext • Find target employees who work with TS • Senior Trader at Stock Company • Works with TS • A+ candidate to phish!
  • 28. Threat Intelligence: Building Pretext Priority Target at Stock Exchange Position Pretext from LinkedIn 1 Rey Oakley Senior Trader Joseph Thompson – Capital Ventures 2 Mike Cortes IT Support Sarah Cho – Computer Stop 3 Karen Hayes Database Admin John Smith – DevShop 4 Stacy Chan Project Manager Mike Jacklin – Logistics R Us • Don’t stop at one, maximize your chances.
  • 29. Handover At this point, the TI Team hands over a “target pack” to the Red Team
  • 33. External Threat: Delivery and Execution • Pretext: Recruitment and Career Opportunities • Delivery: Targeted Phishing (4 users) • Objective: Impact the Integrity of TS 0 1 2 3 4 5 Users Targeted Emails Confirmed Opened Links Clicked Command and Control Obtained Targeted Phishing Statistics
  • 34. External Threat: Execution Execution? Target at Stock Exchange Position Pretext from LinkedIn ý Rey Oakley Senior Trader Joseph Thompson – Capital Ventures ý Mike Cortes IT Support Sarah Cho – Computer Stop þ Karen Hayes Database Admin John Smith – DevShop þ Stacy Chan Project Manager Mike Jacklin – Logistics R Us • Who’s workstation are we on?
  • 35. External Threat: Acting on Objectives Karen Hayes
  • 36. External Threat: Acting on Objectives þ Know where TS Lives þ Know users who access TS Karen Hayes Global File Share TS Documents Active Directory TS Users
  • 37. External Threat: Acting on Objectives Compromised Workstation Trader Workstation
  • 38. External Threat: Acting on Objectives Karen Hayes Karen Hayes Active Directory
  • 39. External Threat: Acting on Objectives Karen Hayes Karen Hayes Citrix User
  • 41. External Threat: Acting on Objectives Karen Hayes Citrix Administrator Workstation Administrator Other Citrix Servers
  • 42. External Threat: Acting on Objectives Compromised Workstation Trader Workstation
  • 43. External Threat: Acting on Objectives Compromised Workstation Trader Workstation Workstation Administrator
  • 44. External Threat: Acting on Objectives Trader Workstation
  • 45.
  • 48. Detection and Response Assessment Outcomes Blue Team had many chances to see what we did. What did they actually see? 1. Ascertain timeline of detected events
  • 49. Detection and Response Assessment Outcomes Blue Team had many chances to see what we did. What did they actually see? 1. Ascertain timeline of detected events 2. How repeatable was the detection method and response? 3. Formal reporting to stakeholders 4. Tools and techniques used in response 5. Lessons learned
  • 50. Detection and Response Assessment Outcomes 1. Attempt to identify weaknesses in people, processes and most importantly technology which is constraining the detection process 2. Identify areas of strength and significant capability 3. Work together to implement and test these changes
  • 52. Conclusion • Test people processes and technology • Test Blue Teams ability to respond to a threat • Not a replacement for penetration testing • Assurance activities should be continuous • Improve security posture
  • 56. Purpose of a Red Team Engagement Holistically test your organisation against a real world breach scenario Strong / Weak Security Posture PROCESS PEOPLE TECHNOLOGY 56 • Measure IR/EDR Capability (Blue Team) • Focus on Depth and not Breadth • Driven from Real World Threats
  • 57. External Threat: Acting on Objectives
  • 58. Why is Red Teaming Important? A few examples where People, Process, and Technology fell down… 58