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Applying Boyd's OODA Loop Strategy to
                    Drive IT Security Decision and Action

                   TK Keanini, Chief Research Officer
                   nCircle




8th Annual GFIRST National Conference, Aug 23, 2012
                    nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Colonel John Boyd (1927 – 1997)
• Fighter Pilot
   – Forty-Second Boyd
• Military Theories
   – Energy Maneuverability Theory
      • Drove requirements for the F15 and F16
   – Discourse on Winning & Losing
   – Destruction & Creation
   – Many modern military strategies based on Boyd
• The OODA Loop
   – the concept that all combat, indeed all human
     competition from chess to soccer to business,
     involves a continuous cycle of Observation,
     Orientation, Decision, and Action
                         nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Simplified OODA in the Context of Time
                             Continuous Monitoring


• Intelligence
   — Observation
   — Orientation

• Execution
   — Decision
   — Action



                   nCircle Company Confidential      © 2012 nCircle. All Rights Reserved.
Feedback Loops of the OODA Loop




               nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Conflict: Red vs. Blue
                                                O     O   D   A




           Blue Ops                                   Red Ops




          A   D   O   O


Problem:
IT has no offense and cannot act on its adversary


                       nCircle Company Confidential               © 2012 nCircle. All Rights Reserved.
OODA for IT Security
                                                    O     O   D   A




                                                          Red Ops

            Blue Ops

       O    O     D    A



        A     D   O    O

    Continuous Monitoring and Rapid Change

                           nCircle Company Confidential               © 2012 nCircle. All Rights Reserved.
Continuous Monitoring/ OODA Loop

• Observation and Orientation (OO) increases
  your perceptive boundaries.
  – Superior Situational Awareness
• Sampling Rate of the OO is relative to the
  rate of change
• Your Decision and Actions should drive your
  rate of change
• Your rate of change should be beyond the
  perceptive boundaries of your adversaries
  Observation and Orientation.
  – Actively monitor for this knowledge margin

                    nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
What is the Objective of your Defensive
Strategy?
The primary objective of your IT strategy is:
A) Business continuity and agility?
B) Catching crooks and crime fighting?


IT Security has no direct
offensive measures so its
dominant strategy must
follow that of a prey species!



How can we raise the cost to our predators/adversaries?
(without raising our own costs)

                                  nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Foraging Patterns of Predator Species
• Cruising (widely foraging)                      Dominant strategy back in the day.
                                                 Servers were the targets and you had
   – Continually move to locate prey                         to find them



• Ambush (sit-and-wait)                          With the proliferation of browsers, the
   – Rely on prey’s mobility to                  prey became mobile and server could
     initiate encounters                                         ambush


• Saltatory (hybrid)
   – Very little exposure when                             Phishing, DNS poisoning, CA
     cruising                                                     spoofing, etc.
   – Cheap ambush resources

                            nCircle Company Confidential                © 2012 nCircle. All Rights Reserved.
Defensive Patterns of Prey Species

• High space and time costs
  – Locations not easily found
  – Location at a high energy cost to predator
• Tolerance
  – Divert the predator to eat non-essential parts
  – Enhanced ability to rapidly recover from the damage
• Befriend your predator's enemy
  – Attract the presence of your predator's predator
• Confrontation
  – Mechanically or chemically


                      nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Anti-Predator Strategies (cost/benefit)
• Cost of identification & misidentification
   • Camouflage
   • Overtly advertise negative benefits
• Cost of attack
   • Energy gained from the kill / energy spent in the hunt
• Cost of handling/ingest
   • Energy spent to convert
   • Lifetime of the gain

 Loss is a part of the design
 The Organism is the target, not the Species

                             nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
The Patterns of a Prey Organism
               Species                                               Service
Organism   Organism   Organism   Organism               Server    Server   Server           Server

• The game of survival and resiliency is at the level
  of species and not at the level of organism
• Diversity, redundancy and a high rate of change at
  the organism level provides stability at the species
  level
• Loss at the organism level is informational
• With no offensive measures, prey must advertise
  unprofitability and raise the cost to its opponent
                                   nCircle Company Confidential            © 2012 nCircle. All Rights Reserved.
Change is Not Happening Fast Enough!
• Server A is configured, tested, and put in to production
• In a 96 hour period, your adversary is able to perform
  enough recon to pick a strategy
• Server A will remain in that original production state
  until
   – A change is required by the business
   – A change is required by the discovery of a vulnerability
   – A change is required by a fault
   – Otherwise, it remains the same for what could be months
     or years (prime real estate for a parasite)
   – Can’t eat just one! What works on A will work on B
     through ‘n’
The adversary will take advantage of the fact that
your cost of change is too high
                        nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Decoupling Organism from Species
Pattern: The abstraction of a [re]source
A few examples include:
Virtual LANS       Logical partitioning of broadcast domains
Virtual Storage    Logical presentation of disks
Virtual Service    Load Balancers, Proxies, etc.
Virtual Machines   VMware, Xen, Microsoft’s Virtual Server, etc




   Advantage: Decoupling
   the resource from the
   source
                            nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Nuke & Pave




What if we could lower the ‘Mean Time to
Recovery’ of the service to seconds?
What if we could change characteristics in the
server while keeping the service the same?
                    nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Orientation: Information Sets




Bob: Targets X


• Ego-centric understanding
 — What you know about your targets




                      nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Orientation: Information Sets




Bob: Targets X                                       Alice: Targets X

Bob: Alice: Targets X                                Alice: Bob: Targets X
Bob: Alice: Bob Targets X


• Allo-centric understanding
 — What you know, what your opponent knows about your
   targets
 — What you know, what your opponent knows, what you know
   about your targets.

                            nCircle Company Confidential                © 2012 nCircle. All Rights Reserved.
The cost of your adversaries Observation and
Orientation (OO)
• Your common target attributes
• Your common practices
• Your High Cost of Change: MTTR (Mean Time to
  Repair) or TTM (Time to Manufacture)
• How can we lower the effectiveness of their tools or
  process?
• How can we raise their costs?


                       nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Knowledge Margin


dT arg et dAdversaryObservation
         
 dTime           dTime
“If a target system can cause the adversary to
 constantly have to recompute their tactics, to
 cause uncertainty on the adversary's causal
models, they can achieve a knowledge margin
     that is feasible and sustainable.” - TK

                   nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Creating a Knowledge Margin


• Leverage virtualization for synthetic provisioning
• Ability to provision the entire ‘backend’ on a per
  session basis
• Continuously monitor for diversity without adding
  administrative costs




                      nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Example: Synthetic Provisioning


User A            User B              User C
JIT Services A    JIT Services B       JIT Services C                   Service


             Specifications & Jitter


             Virtual       Virtual         vLAN                Server    Server            Server
  Virtual
 Storage    Machines       CPUs            MPLS

             Specifications & Jitter

                 CPU       OS                 LAN
 Storage                                                               Physical
                 Memory                      WAN                    Infrastructure

                                nCircle Company Confidential            © 2012 nCircle. All Rights Reserved.
Continuous Monitoring/ OODA Loop
Summary
• We must find a way to raise the cost to our
  adversary while not raising our own administrative
  costs
• Observation and Orientation (OO) increases your
  perceptive boundaries.
• Sampling Rate of the OO is relative to the rate of
  change
• Your Decision and Actions should drive your rate of
  change
   – Proactively introduce change at the server level while
     holding to your service level agreements
• Your rate of change should be beyond the perceptive
  boundaries of your adversaries Observation and
  Orientation.
   – Actively monitor for this knowledge margin
                         nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.
Contact




Twitter: @tkeanini
Email: tk@ncircle.com
Linkedin: http://www.linkedin.com/in/tkkeaninipub

                    nCircle Company Confidential   © 2012 nCircle. All Rights Reserved.

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Applying Boyd's OODA Loop Strategy to Drive IT Security Decision and Action

  • 1. Applying Boyd's OODA Loop Strategy to Drive IT Security Decision and Action TK Keanini, Chief Research Officer nCircle 8th Annual GFIRST National Conference, Aug 23, 2012 nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 2. Colonel John Boyd (1927 – 1997) • Fighter Pilot – Forty-Second Boyd • Military Theories – Energy Maneuverability Theory • Drove requirements for the F15 and F16 – Discourse on Winning & Losing – Destruction & Creation – Many modern military strategies based on Boyd • The OODA Loop – the concept that all combat, indeed all human competition from chess to soccer to business, involves a continuous cycle of Observation, Orientation, Decision, and Action nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 3. Simplified OODA in the Context of Time Continuous Monitoring • Intelligence — Observation — Orientation • Execution — Decision — Action nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 4. Feedback Loops of the OODA Loop nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 5. Conflict: Red vs. Blue O O D A Blue Ops Red Ops A D O O Problem: IT has no offense and cannot act on its adversary nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 6. OODA for IT Security O O D A Red Ops Blue Ops O O D A A D O O Continuous Monitoring and Rapid Change nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 7. Continuous Monitoring/ OODA Loop • Observation and Orientation (OO) increases your perceptive boundaries. – Superior Situational Awareness • Sampling Rate of the OO is relative to the rate of change • Your Decision and Actions should drive your rate of change • Your rate of change should be beyond the perceptive boundaries of your adversaries Observation and Orientation. – Actively monitor for this knowledge margin nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 8. What is the Objective of your Defensive Strategy? The primary objective of your IT strategy is: A) Business continuity and agility? B) Catching crooks and crime fighting? IT Security has no direct offensive measures so its dominant strategy must follow that of a prey species! How can we raise the cost to our predators/adversaries? (without raising our own costs) nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 9. Foraging Patterns of Predator Species • Cruising (widely foraging) Dominant strategy back in the day. Servers were the targets and you had – Continually move to locate prey to find them • Ambush (sit-and-wait) With the proliferation of browsers, the – Rely on prey’s mobility to prey became mobile and server could initiate encounters ambush • Saltatory (hybrid) – Very little exposure when Phishing, DNS poisoning, CA cruising spoofing, etc. – Cheap ambush resources nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 10. Defensive Patterns of Prey Species • High space and time costs – Locations not easily found – Location at a high energy cost to predator • Tolerance – Divert the predator to eat non-essential parts – Enhanced ability to rapidly recover from the damage • Befriend your predator's enemy – Attract the presence of your predator's predator • Confrontation – Mechanically or chemically nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 11. Anti-Predator Strategies (cost/benefit) • Cost of identification & misidentification • Camouflage • Overtly advertise negative benefits • Cost of attack • Energy gained from the kill / energy spent in the hunt • Cost of handling/ingest • Energy spent to convert • Lifetime of the gain Loss is a part of the design The Organism is the target, not the Species nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 12. The Patterns of a Prey Organism Species Service Organism Organism Organism Organism Server Server Server Server • The game of survival and resiliency is at the level of species and not at the level of organism • Diversity, redundancy and a high rate of change at the organism level provides stability at the species level • Loss at the organism level is informational • With no offensive measures, prey must advertise unprofitability and raise the cost to its opponent nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 13. Change is Not Happening Fast Enough! • Server A is configured, tested, and put in to production • In a 96 hour period, your adversary is able to perform enough recon to pick a strategy • Server A will remain in that original production state until – A change is required by the business – A change is required by the discovery of a vulnerability – A change is required by a fault – Otherwise, it remains the same for what could be months or years (prime real estate for a parasite) – Can’t eat just one! What works on A will work on B through ‘n’ The adversary will take advantage of the fact that your cost of change is too high nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 14. Decoupling Organism from Species Pattern: The abstraction of a [re]source A few examples include: Virtual LANS Logical partitioning of broadcast domains Virtual Storage Logical presentation of disks Virtual Service Load Balancers, Proxies, etc. Virtual Machines VMware, Xen, Microsoft’s Virtual Server, etc Advantage: Decoupling the resource from the source nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 15. Nuke & Pave What if we could lower the ‘Mean Time to Recovery’ of the service to seconds? What if we could change characteristics in the server while keeping the service the same? nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 16. Orientation: Information Sets Bob: Targets X • Ego-centric understanding — What you know about your targets nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 17. Orientation: Information Sets Bob: Targets X Alice: Targets X Bob: Alice: Targets X Alice: Bob: Targets X Bob: Alice: Bob Targets X • Allo-centric understanding — What you know, what your opponent knows about your targets — What you know, what your opponent knows, what you know about your targets. nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 18. The cost of your adversaries Observation and Orientation (OO) • Your common target attributes • Your common practices • Your High Cost of Change: MTTR (Mean Time to Repair) or TTM (Time to Manufacture) • How can we lower the effectiveness of their tools or process? • How can we raise their costs? nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 19. Knowledge Margin dT arg et dAdversaryObservation  dTime dTime “If a target system can cause the adversary to constantly have to recompute their tactics, to cause uncertainty on the adversary's causal models, they can achieve a knowledge margin that is feasible and sustainable.” - TK nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 20. Creating a Knowledge Margin • Leverage virtualization for synthetic provisioning • Ability to provision the entire ‘backend’ on a per session basis • Continuously monitor for diversity without adding administrative costs nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 21. Example: Synthetic Provisioning User A User B User C JIT Services A JIT Services B JIT Services C Service Specifications & Jitter Virtual Virtual vLAN Server Server Server Virtual Storage Machines CPUs MPLS Specifications & Jitter CPU OS LAN Storage Physical Memory WAN Infrastructure nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 22. Continuous Monitoring/ OODA Loop Summary • We must find a way to raise the cost to our adversary while not raising our own administrative costs • Observation and Orientation (OO) increases your perceptive boundaries. • Sampling Rate of the OO is relative to the rate of change • Your Decision and Actions should drive your rate of change – Proactively introduce change at the server level while holding to your service level agreements • Your rate of change should be beyond the perceptive boundaries of your adversaries Observation and Orientation. – Actively monitor for this knowledge margin nCircle Company Confidential © 2012 nCircle. All Rights Reserved.
  • 23. Contact Twitter: @tkeanini Email: tk@ncircle.com Linkedin: http://www.linkedin.com/in/tkkeaninipub nCircle Company Confidential © 2012 nCircle. All Rights Reserved.