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How to Plan Purple Team Exercises

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Haydn Johnson
Haydn Johnson

Purple Teaming is the idea of using a Red Team exercise with clear training objectives for the Blue Team. Great exercises should not just be focused on testing a product, they should also test your active Blue Team members and their skills. But how does one start to think about a Purple Team exercise, how does one go about running one and what does it look like? In this talk we will explain what, why and how, to plan an effective purple team exercise and give some examples. Most enterprise networks are Windows heavy so examples will heavily lean on this. Testing Assumptions, gaps, blind spots is what being proactive is all about. This talk is both for the console folks and non-console folks.

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@haydnjohnson How to Plan a Purple Team Exercise!
@haydnjohnson Haydn Johnson ◈ Security Consultant - Researcher ◈ @haydnjohnson ◈ Talks: BsidesTO, Circle City Con, HackFest, SecTor ◈ Offsec, Purple Team, Gym?? ◈ http://www.slideshare.net/HaydnJohnson Australian living in Canada
@haydnjohnson Back to the Talk Let’s start with the first set of slides
@haydnjohnson Planning a Purple Team Exercise 0
@haydnjohnson Outline Terminology RedBlue History Lesson Purple Team Story Time Cyber Exercises
@haydnjohnson “ SOME SUN TZU Quote, because l33t Red team hackers
@haydnjohnson Terminology 1
@haydnjohnson Red Team 1
@haydnjohnson Red Team Vulnerability Assessment Person Run Vuln Scanner….hey client you suck Penetration Tester Metasploit /MSF PRO (FTW)...hey client you suck
@haydnjohnson Red Team Red Teaming Phish, move laterally, find “sensitive stuff”, maybe custom implant...hey client you suck
@haydnjohnson Blue Team 1
@haydnjohnson Blue Team ◈Support ◈Firewalls | Blinky Boxes ◈Threat Intel
@haydnjohnson ◈ Identify ◈ Confirm ◈ Respond Blue Team ◈ Mitigate ◈ Remove ◈ Improve
@haydnjohnson Purple Team 1
@haydnjohnson Purple Team Togetherness
@haydnjohnson Purple Team Togetherness
@haydnjohnson Purple Team ◈Red and Blue working Together ◈Symbiotic ◈Beneficial
@haydnjohnson Purple Team Working together to achieve the ultimate goal of making the organization more secure ◈different threats & attacker mindset ◈incident detection and response ◈policy and procedures ◈tuning of controls Benefits
@haydnjohnson History Lesson Red Team Origin == #Purple Team 2
@haydnjohnson
@haydnjohnson Red Team Origin We (Red Team) f*cked up so badly. We had to create a term to remind you (Blue Team), that we are there to help you…. Not just beat you up.
@haydnjohnson RedTeams.net - Definition
@haydnjohnson “capabilities evolved and they turned into a force tasked with challenging the security posture of military bases..” http://redteams.net/blog/2013/what-is-a-red-team RedTeams.net - Definition
@haydnjohnson “A key aspect of the red team operations today is the adversarial way of thinking, the “Red Team Mindset”. Red team members think outside the box…” http://redteams.net/blog/2013/what-is-a-red-team https://blog.cobaltstrike.com/2015/04/29/2015s-red-team-tradecraft/ RedTeams.net - Defnition
@haydnjohnson I Love Purple Team: Collaboration. https://blog.cobaltstrike.com/2014/11/12/adversary-simulation-becomes-a-thing/
@haydnjohnson Red Team
@haydnjohnson
@haydnjohnson Cyber Exercises The foundations 3
@haydnjohnson Objectives Foundation Cyber Exercises
@haydnjohnson Outcomes Cyber Exercises Foundation
@haydnjohnson Event / Injects Events - generally executed by the Red Team to elicit responses from the Blue Team in specific phases, focused on the objectives of the exercise. Cyber Exercises Terms
@haydnjohnson Cyber Exercises Teams 3
@haydnjohnson Cyber Exercises Teams RED BLUE GREYECG
@haydnjohnson ECG Grey Cell Director Team Lead Eyes and Ears Cyber ExercisesGREY
@haydnjohnson Green Cell GREY IR Manager Team Lead Director Cyber ExercisesECG
@haydnjohnson Cyber Exercises Phases 3
@haydnjohnson Cyber Exercises ◈Plan Phases ◈Execution ◈Lessons Learned https://www.mitre.org/sites/default/files/publications/pr_14-3929-cyber-exercise-playbook.pdf
@haydnjohnson Cyber Exercises Planning Preliminary Meeting Middle Meeting (s) Final Meeting
@haydnjohnson Cyber Exercises Planning ◈Concept Meeting ◈Brainstorming ◈Sticky notes!
@haydnjohnson Cyber Exercises Ideas ◈ Visibility ◈ Test assumption ◈ Budget ◈ Initial Weakness ◈ New technology ◈ New Team
@haydnjohnson Cyber Exercises Planning https://www.fireeye.com/blog/threat-research/2014/10/apt28-a-window-into-russias- cyber-espionage-operations.html
@haydnjohnson
@haydnjohnson Cyber Exercises Planning ◈ Middle Planning Meetings ◈Action Items ◈Accountability
@haydnjohnson Cyber Exercises Ideas ◈Prevent confusion ◈Finalize Objectives ◈Preliminary recon ◈Who to involve ◈Use Case ◈Training Required
@haydnjohnson Cyber Exercises Planning ◈ Final stage Meetings ◈Cross the T’s ◈Dot the I’s
@haydnjohnson Cyber Exercises Ideas
@haydnjohnson Cyber Exercises Ideas
@haydnjohnson Cyber Exercises Outcomes
@haydnjohnson Cyber Exercises Execution Execute the exercise Observe, observe, observe!
@haydnjohnson Exercise Control Group Red Team Training Audience Observers RT tasked with action 1
@haydnjohnson Exercise Control Group Red Team Training Audience Observers RT tasked with action 1 Execute Inject /Event 2
@haydnjohnson Exercise Control Group Red Team Training Audience Observers RT tasked with action 1 Execute Inject /Event 2 Collects information 3
@haydnjohnson Exercise Control Group Red Team Training Audience Observers RT tasked with action 1 Execute Inject /Event 2 Collects information 3 4 Feedback to ECG
@haydnjohnson Exercise Control Group Red Team Training Audience Observers RT tasked with action 1 Execute Inject /Event 2 Collects information 3 Tasked with action 4 Feedback to ECG
@haydnjohnson Cyber Exercises Execution No alerts No response GREY
@haydnjohnson Exercise Control Group Red Team Training Audience Observers !Check for Domain hackers.fu
@haydnjohnson Exercise Control Group Red Team Training Audience Observers Check for AV log / alert for mal.exe !
@haydnjohnson Cyber Exercises Execution Follow through on planning
@haydnjohnson Cyber Exercises Execution Take Note: How is the team responding What problems ? Bottlenecks?
@haydnjohnson Cyber Exercises Lessons Learned What observations were made during the exercise. What went well… or what didn’t Positive and negative - constructive
@haydnjohnson Bad Good Exercise Follow-upImprovements
@haydnjohnson Exercise Control Group Red Team Training Audience Observers Collect information Strengthen future exercises
@haydnjohnson Purple Team It Planning 4
@haydnjohnson Purple Team it Start Small Do not bite off more than you can chew. Consider : Funding / Budget Support Skills Technology
@haydnjohnson Purple Team it What do you have Is your security budget YUUGE? Do you have threat hunting? It’s the best. Do you have a blinky box! Sad!
@haydnjohnson Purple Team It SDLC / Security Program Is it mature? Is there one? What things annoy the team?
@haydnjohnson Purple Team It The paper based one Example: Testing Processes
@haydnjohnson Purple Team It Testing Processes Temporary Access Card
@haydnjohnson Purple Team It Testing Processes What is required to get one A signature? Evidence of identity
@haydnjohnson Purple Team It Testing Processes What if it is not approved? Fake signature?
@haydnjohnson Purple Team It Testing Processes Ask questions If an employee loses a card, what happens.
@haydnjohnson Purple Team It Testing Processes Red Team It Try to get a pass without approval Not the normal process
@haydnjohnson Purple Team It Start with the Basics Example: Detecting Port Scanning https://www.safaribooksonline.com/library/view/snort-cookbook/0596007914/ch04s06.html
@haydnjohnson Purple Team It Port Scanning Pentester run Nmap internally… Can be that simple!
@haydnjohnson Purple Team It Port Scanning ◈Increase in complexity ◈Slower scan ◈Fragmented scan
@haydnjohnson
@haydnjohnson Purple Team It Nmap - u wot m8? But APT! APT won’t use NMAP It is a start Tests current technology Simple Relatively cheap
@haydnjohnson Try - PowerShell Purple Team It
@haydnjohnson Purple Team It Example: Restricted Desktop Environments https://www.safaribooksonline.com/library/view/snort-cookbook/0596007914/ch04s06.html
@haydnjohnson Purple Team it Restricted Desktop Environments Organisations have lost control of their data
@haydnjohnson https://technet.microsoft.com/en-us/library/bb457006.aspx#ENAA secpol.msc
@haydnjohnson https://technet.microsoft.com/en- us/library/bb457006.aspx#ENAA
@haydnjohnson Restrict Drives!
@haydnjohnson Restrict Drives!
@haydnjohnson No C Drive!
@haydnjohnson Full Path
@haydnjohnson Run cmd.exe
@haydnjohnson cmd 4 u
@haydnjohnson Prevent cmd.exe access directly
@haydnjohnson No CMD 4 u
@haydnjohnson Purple Team It Example: Applocker
@haydnjohnson LSP for everyone
@haydnjohnson Applocker Enabled
@haydnjohnson Payload Blocked
@haydnjohnson Compile with .Net on Host csc.exe /unsafe /platform:x86 /out:bp2.exe .beaconPayload.cs
@haydnjohnson Execute with InstallUtil on Host Installutil.exe /logfile= /logtoconsole=false /U .bp.exe
@haydnjohnson Receive connection
@haydnjohnson Purple Team Ideas People Process Technology Skillset Mean time to detection Use of Tools Attacker mindset Paperwork Reporting Escalation Firewall Anti Virus Whitelisting TTP Pyramid of pain
@haydnjohnson STORY TIME BANK RED TEAM 4
@haydnjohnson @carnal0wnage Story Time Privilege Escalation Assume Breach Meterpreter C2 Exfiltration - FTP “Red Team” @ $canadian Bank
@haydnjohnson @carnal0wnage Story Time Receive call “Check this IP address” $secretpoliceinvestigation IP address seen - Investigators go to meeting + lunch 2 hours later, identify data exfil Sh*t hits fan Log into FTP server to delete data Execute processes Alerts triggered purposely
@haydnjohnson @carnal0wnage Story Time Debrief Red TeamBlue Team What we saw What was done The GAP Improvements ==
@haydnjohnson @carnal0wnage Story Time Process not as effective as it looks Road Blocks in communication Lessons learned
@haydnjohnson @carnal0wnage Story Time Process bypassed Hard to collaborate Rotating Shifts Lessons learned
@haydnjohnson @carnal0wnage Story Time IR equipment == slow Infrastructure out of date Lessons learned
@haydnjohnson @carnal0wnage Story Time Big company hard to change quickly Issues clearly acknowledged Long term plans Nothing changed in short term
@haydnjohnson @carnal0wnage Story Time Create defined and clear process for hierarchy Training on hacking back - DON’T Budget for prioritized upgrade of Lab Shift style lunches Solutions
@haydnjohnson Conclusion 5 Almost the end
@haydnjohnson Purple Team it What to take away Don’t assume Be proactive Take action
@haydnjohnson Purple Team it Thank you Debate, discuss, questions Now | Afterwards I Twitter | Pub @haydnjohnson
@haydnjohnson References ◈https://medium.com/@lennartkoopmann/explain ing-and-adapting-tays-sysmon-configuration- 27d9719a89a8#.fsvuszvp3

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