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Adversarial Modeling Exercises
Simulation
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
HI…I’m Chris
and…I’m Chris
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
•  Cursing
•  Racism
•  Religious Prejudice
•  Sex
•  Drugs
•  Daddy / Abandonment issues
•  Socio Economic Hate crimes
•  Thin Skin
•  Lack of sense of humor
•  Sexual orientation
•  Sexism
•  Violence
•  Vomiting
•  Abuse
• Truth
• Fear
• Honesty
• Facts
• Emotions
• Opinions
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Chris Gates - Sr. Incident Response Engineer - Uber
Twitter: @carnal0wnage
Blog: carnal0wnage.attackresearch.com
Talks: slideshare.net/chrisgates
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
http://www.pentest-standard.org/
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
A story
•  Got Red Teamed at work
•  It was not fun
•  I’m usually the person bringing the pain, not receiving it
•  Tons of thoughts and emotions
A story
Initially
A story
Then… reflection
A story
Then… realization
•  I was probably that a$$hole on the phone
•  Actually, I’m sure of it
•  Super difficult to give valid recommendations in a
generic way
•  I’m blind to internal processes, roadmaps, politics
A story
We give recommendations like these:
A story
•  Do a bunch of complex recommendations, then you’ll
be “secure”
•  Most org fail at the basics, but basics aren’t sexy
•  In fact tell an org they need to do a bunch of basic
hardening and see if you get follow-on work
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Problems With Testing Today
•  Limited metrics
•  Increased Tech debt
•  Fracturing of TEAM mentality
•  Looks NOTHING like an attack
•  Gives limited experience
•  Is a step above Vuln Assessment
•  Is NOT essential to the success of the
organization
•  Is REALLY just a glorified internal pentest
team
Building a successful internal
Adversarial Simulation Team
Easy!
Standard players: (limited scope, limited flexibility)
Step #1: Get people who can do the hack
Step #1.5: Complain about the scope
Step #2: Hack all the things!
Step #3: Write up stuff to tell people why the hax iz bad.
Advanced players: ( increased scope and flexibility)
Step #4: Tell Defense Team how u did hax
Step #5: Defense team does defensive’y stuff or blames
team that refuses to patch the thing
Step #6: repeat
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Terminology:
Gotta get a few things straight first
•  We keep screwing up terms
•  Vulnerability Assessment person ( U ran a Vuln
scanner?)
•  Penetration Tester ( U hit autopwn)
•  Red Teamer ( U hit autopwn and moved laterally?
Maybe even found “sensitive stuff”)
•  Purple Teamer (U did all of the above but charged
more to talk with the defense teams during the test)
•  ADVERSARIAL ENGINEER (U exist to simulate real
world TTP’s, generate experience, and provide
metric scoring of corporate readiness/resistance to
attack)
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
https://attack.mitre.org/wiki/Main_Page
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
#1 You need a charter and a
Problem statement
Charter
•  Analyze real world threats against $Company.
•  Develop attack models which validate our detection
capabilities.
•  Validate our detection, prevention, and response
against real world threats.
•  Provide metrics around $Company’s corporate readiness/
resistance to various attacks across a broad set of threat
tactics, techniques, and procedures (TTPs)  via table top
exercises, automated, and manual testing.
•  GOAL: Predict likelihood of successful attacks before they
happen
#2 Define how you will
accomplish solving the
problem and how the
team will get/consume
projects
Red	Team
Management
Blue	Team
Add	Item	to	
Concerns	List
Collaboration,	
Prioritization,	and	
Sequencing	Meeting
Categorize	Type	of	
Work	and	Time	
Requirement.	
Penetration	
Testing	and	
Adversary	
Simulation	
Assessment	
(Full	or	Mini)
TTP	Replay
Consulting	and	
Assistance
Assign	Work	to	
appropriate	
resources
Summarize,	
Document,	and	
Report	Findings
Update	Internal	
Documentation,	
Processes,	and	
Methodology
Threat	Intel
New	Vuln
or	Technique?
Enter	into	Vuln	DBVuln?
Enter	into	Matrix
Technique? End
Gather	Budget	
Information	and	
Approvals
Notify	affected	
groups	of	requested	
work	and	expected	
timeline
Update	Attack	Wiki
TTP	Matrix
#3 Create a repeatable
strategy for execution of
simulations
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
•  Unit testing for you detection rules
•  You don’t deploy untested code to prod do you?
•  Automate attacks and verify responses
Example
Example
Example
#4 Creation of an information sharing
platform and knowledgebase
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
#5 Assemble your team and tools
Think ahead, This is not your normal pentest team!
•  Servers
•  Storage
•  Hardware
•  Tools
•  Implants
•  Customizations
•  Virtualization infrastructure
•  Access to all defensive tools
•  Built out lab environments to recreate / replicate
•  Cracking Rigs and more…
#6 Create formal collateral
•  Introduction of the team and it’s capabilities
•  Services Line Card
•  Engineering bios and availability
•  Scoping documentation/questionnaires
•  Rules of engagement
•  Internal information handling policy, procedure,
process
•  Engagement request process
•  Defensive Team Collaboration Workflow
•  Threat Intel Team Collaboration Workflow
•  Approval notification Protocols
•  Templated / Automated reporting output
•  Team Member Skill matrix
#7 Defensive Coverage
Assessment
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
#8 Provide Metrics that
evaluate each TTP from a
protective, detective and
response perspective
Color	Key:	 Detec-on	Maturity	 Protec-on	Maturity	
0	
No	Detec-on	Controls	 No	Protec-on	Controls	
1	
Non-Centralized	Logging	 Par-ally	Deployed	
2	
Centralized	Logging,	but	no	Alerts	 Fully	Deployed	but	Defeatable	
3	Centralized	Logs,	Reac-ve,	Insufficient	Alerts,	
false	nega-ves	or	posi-ves	(Func-onal)	 Fully	Deployed,	Non-Defeatable	
4	Centralized,	Automated	Alerts,	Proac-ve,	
Requires	response,	no	false	posi-ves	(Stable)	
Fully	Deployed,	Non-Defeatable,	and	
Aler-ng	in	place
Technique	 Func0on	 Methods	for	detec0on	 Methods	for	protec0on	 Detec0on	 Mat
urity	
Protec0on	 Mat
urity	
Last	Test	
Date	
LSASS	password/
hash	recovery	
Local	Security	
Authority	Subsystem	
Service	(LSASS)	is	a	
process	in	MicrosoH	
Windows	opera0ng	
systems	that	is	
responsible	for	
enforcing	the	security	
policy	on	the	system.	
It	verifies	users	
logging	on	to	a	
Windows	computer	or	
server,	handles	
password	changes,	
and	creates	access	
tokens.	(from	
Wikipedia)	
	
For	the	purposes	of	
Single	Sign	On	(SSO)	in	
Windows	
environments,	lsass	
also	stores	the	NT	
hash	and	some0mes,	
in	the	case	of	wdigest,	
the	cleartext	
creden0als	of	users	
who	have	logged	into	
the	system.	These	can	
be	recovered	by	
dumping	the	contents	
of	the	process	in	
memory	through	use	
tools	such	as	
procdump	and	
mimikatz.		
The	most	op0mal	way	to	detect	this	is	to	
iden0fy	processes	that	are	crossproc'd	
into	lsass.	The	signal	to	noise	ra0o	here	is	
high,	due	to	the	nature	of	lsass'	func0on.	
	
Typically	meterpreter	uses	rundll32	to	
run,	so	iden0fying	rundll32	into	lsass	
along	with	processes	injected	into	
winlogon	that	cross	process	into	lsass	will	
reliably	iden0fy	malicious	ac0vity	
An	automated	password	management	
tool	such	as	CyberArk	can	be	used	to	
randomize	passwords	and	change	them	
aHer	every	use,	thus	decreasing	the	
efficacy	of	mimikatz	as	any	recovered	
creden0al	will	likely	be	expired.	
	
Further,	on	all	windows	8/2012+	desktops	
and	servers,	wdigest	should	be	disabled	in	
accordance	with	the	following	KB	ar0cle	
from	MicrosoH:	
h]ps://support.microsoH.com/en-us/kb/
2871997	
	
Enforcing	the	principle	of	Least	User	
Access	will	also	help	mi0gate	the	
effec0veness	of	mimikatz	as	it	will	limit	
the	access	provided	by	the	compromised	
creden0als.	
	
Lastly,	adding	some	form	of	Two	Factor	
Authen0ca0on,	such	as	smart	cards,	can	
further	limit	the	usefulness	of	the	
recovered	creden0als.	
Rules	wri]en	
in	carbon	
black	to	detect	
cross	process	
ac0vity	from	
rundll32	into	
lsass	
	
Rule	wri]en	to	
iden0fy	
PowerShell	
crossproc	into	
lsass.	
	
Addi0onal	rule	
wri]en	to	
detect	an	
injected	
process	into	
winlogon	with	
cross	process	
ac0vity	into	
lsass	
	
.	
32FA	(user-land	
only),	some	
CyberArk	
usage,	some	
creden0als	
flushed	every	
24	hours	
1
4/7/2016
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
#9 Evaluate adversarial
skill to determine urgency
of simulation
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
#10 Re-prioritize workload of
Adversarial team based on
TTP last test date (decay) or
based on other external
drivers (ex. TTP is used in a
current attack campaign)
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
#11 Defensive Measurement
Now that we have measured RT ability to conduct attacks
Now we need to gather defensive metrics
•  Total Coverage
•  Mean Time to Detection
•  Mean Time to Remediation
•  % Successful Eradication
•  Protection Metrics
•  Automated vs Manual Detection
•  Automated vs Manual Response
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Adversarial Simulation Dashboard
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson
Total Protection/Detection/Response
Potential P/D/R
Actual P/D/R
$Company asks “What do we do next, buy more
stuff?”
Execution Gap Coverage
Gap
Future Work
The Future
•  Automate Red Team / Blue Team correlation
•  Automate Attack Path simulation
•  Predict impact of new attacks without running them
•  Predicting probability of attack chains
•  Reduced risk testing model
•  Zero testing debt
•  Response metrics via API queries of security tooling
•  Tracking defensive TTPs
•  Understand how all security tooling come together
Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson

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Building a Successful Internal Adversarial Simulation Team - Chris Gates & Chris Nickerson

  • 1. aka: Some new term to use because we keep screwing up terminology and treating people like children with a crayon box Adversarial Modeling Exercises Simulation
  • 6. •  Cursing •  Racism •  Religious Prejudice •  Sex •  Drugs •  Daddy / Abandonment issues •  Socio Economic Hate crimes •  Thin Skin •  Lack of sense of humor •  Sexual orientation •  Sexism •  Violence •  Vomiting •  Abuse • Truth • Fear • Honesty • Facts • Emotions • Opinions
  • 9. Chris Gates - Sr. Incident Response Engineer - Uber Twitter: @carnal0wnage Blog: carnal0wnage.attackresearch.com Talks: slideshare.net/chrisgates
  • 19. A story •  Got Red Teamed at work •  It was not fun •  I’m usually the person bringing the pain, not receiving it •  Tons of thoughts and emotions
  • 22. A story Then… realization •  I was probably that a$$hole on the phone •  Actually, I’m sure of it •  Super difficult to give valid recommendations in a generic way •  I’m blind to internal processes, roadmaps, politics
  • 23. A story We give recommendations like these:
  • 24. A story •  Do a bunch of complex recommendations, then you’ll be “secure” •  Most org fail at the basics, but basics aren’t sexy •  In fact tell an org they need to do a bunch of basic hardening and see if you get follow-on work
  • 26. Problems With Testing Today •  Limited metrics •  Increased Tech debt •  Fracturing of TEAM mentality •  Looks NOTHING like an attack •  Gives limited experience •  Is a step above Vuln Assessment •  Is NOT essential to the success of the organization •  Is REALLY just a glorified internal pentest team
  • 27. Building a successful internal Adversarial Simulation Team
  • 28. Easy! Standard players: (limited scope, limited flexibility) Step #1: Get people who can do the hack Step #1.5: Complain about the scope Step #2: Hack all the things! Step #3: Write up stuff to tell people why the hax iz bad. Advanced players: ( increased scope and flexibility) Step #4: Tell Defense Team how u did hax Step #5: Defense team does defensive’y stuff or blames team that refuses to patch the thing Step #6: repeat
  • 30. Terminology: Gotta get a few things straight first •  We keep screwing up terms •  Vulnerability Assessment person ( U ran a Vuln scanner?) •  Penetration Tester ( U hit autopwn) •  Red Teamer ( U hit autopwn and moved laterally? Maybe even found “sensitive stuff”) •  Purple Teamer (U did all of the above but charged more to talk with the defense teams during the test) •  ADVERSARIAL ENGINEER (U exist to simulate real world TTP’s, generate experience, and provide metric scoring of corporate readiness/resistance to attack)
  • 35. #1 You need a charter and a Problem statement
  • 36. Charter •  Analyze real world threats against $Company. •  Develop attack models which validate our detection capabilities. •  Validate our detection, prevention, and response against real world threats. •  Provide metrics around $Company’s corporate readiness/ resistance to various attacks across a broad set of threat tactics, techniques, and procedures (TTPs)  via table top exercises, automated, and manual testing. •  GOAL: Predict likelihood of successful attacks before they happen
  • 37. #2 Define how you will accomplish solving the problem and how the team will get/consume projects
  • 39. #3 Create a repeatable strategy for execution of simulations
  • 42. •  Unit testing for you detection rules •  You don’t deploy untested code to prod do you? •  Automate attacks and verify responses
  • 46. #4 Creation of an information sharing platform and knowledgebase
  • 48. #5 Assemble your team and tools Think ahead, This is not your normal pentest team! •  Servers •  Storage •  Hardware •  Tools •  Implants •  Customizations •  Virtualization infrastructure •  Access to all defensive tools •  Built out lab environments to recreate / replicate •  Cracking Rigs and more…
  • 49. #6 Create formal collateral •  Introduction of the team and it’s capabilities •  Services Line Card •  Engineering bios and availability •  Scoping documentation/questionnaires •  Rules of engagement •  Internal information handling policy, procedure, process •  Engagement request process •  Defensive Team Collaboration Workflow •  Threat Intel Team Collaboration Workflow •  Approval notification Protocols •  Templated / Automated reporting output •  Team Member Skill matrix
  • 52. #8 Provide Metrics that evaluate each TTP from a protective, detective and response perspective
  • 53. Color Key: Detec-on Maturity Protec-on Maturity 0 No Detec-on Controls No Protec-on Controls 1 Non-Centralized Logging Par-ally Deployed 2 Centralized Logging, but no Alerts Fully Deployed but Defeatable 3 Centralized Logs, Reac-ve, Insufficient Alerts, false nega-ves or posi-ves (Func-onal) Fully Deployed, Non-Defeatable 4 Centralized, Automated Alerts, Proac-ve, Requires response, no false posi-ves (Stable) Fully Deployed, Non-Defeatable, and Aler-ng in place
  • 54. Technique Func0on Methods for detec0on Methods for protec0on Detec0on Mat urity Protec0on Mat urity Last Test Date LSASS password/ hash recovery Local Security Authority Subsystem Service (LSASS) is a process in MicrosoH Windows opera0ng systems that is responsible for enforcing the security policy on the system. It verifies users logging on to a Windows computer or server, handles password changes, and creates access tokens. (from Wikipedia) For the purposes of Single Sign On (SSO) in Windows environments, lsass also stores the NT hash and some0mes, in the case of wdigest, the cleartext creden0als of users who have logged into the system. These can be recovered by dumping the contents of the process in memory through use tools such as procdump and mimikatz. The most op0mal way to detect this is to iden0fy processes that are crossproc'd into lsass. The signal to noise ra0o here is high, due to the nature of lsass' func0on. Typically meterpreter uses rundll32 to run, so iden0fying rundll32 into lsass along with processes injected into winlogon that cross process into lsass will reliably iden0fy malicious ac0vity An automated password management tool such as CyberArk can be used to randomize passwords and change them aHer every use, thus decreasing the efficacy of mimikatz as any recovered creden0al will likely be expired. Further, on all windows 8/2012+ desktops and servers, wdigest should be disabled in accordance with the following KB ar0cle from MicrosoH: h]ps://support.microsoH.com/en-us/kb/ 2871997 Enforcing the principle of Least User Access will also help mi0gate the effec0veness of mimikatz as it will limit the access provided by the compromised creden0als. Lastly, adding some form of Two Factor Authen0ca0on, such as smart cards, can further limit the usefulness of the recovered creden0als. Rules wri]en in carbon black to detect cross process ac0vity from rundll32 into lsass Rule wri]en to iden0fy PowerShell crossproc into lsass. Addi0onal rule wri]en to detect an injected process into winlogon with cross process ac0vity into lsass . 32FA (user-land only), some CyberArk usage, some creden0als flushed every 24 hours 1 4/7/2016
  • 58. #9 Evaluate adversarial skill to determine urgency of simulation
  • 61. #10 Re-prioritize workload of Adversarial team based on TTP last test date (decay) or based on other external drivers (ex. TTP is used in a current attack campaign)
  • 63. #11 Defensive Measurement Now that we have measured RT ability to conduct attacks Now we need to gather defensive metrics •  Total Coverage •  Mean Time to Detection •  Mean Time to Remediation •  % Successful Eradication •  Protection Metrics •  Automated vs Manual Detection •  Automated vs Manual Response
  • 70. Total Protection/Detection/Response Potential P/D/R Actual P/D/R $Company asks “What do we do next, buy more stuff?” Execution Gap Coverage Gap
  • 72. The Future •  Automate Red Team / Blue Team correlation •  Automate Attack Path simulation •  Predict impact of new attacks without running them •  Predicting probability of attack chains •  Reduced risk testing model •  Zero testing debt •  Response metrics via API queries of security tooling •  Tracking defensive TTPs •  Understand how all security tooling come together