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Of security testing and assessment
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Pain in the arse
Loudmouth
Hacker Punk
Tells lies (professionally)
Is called all sorts of bad words.. That I will likely say
throughout this talk
Cant code well
Talks $hit
Drinks a LOT
Is an overall J3rk
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
LARES
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
OSINT
SIGINT
TSCM/ Bug Sweeping
Exploit Development
Tool Creation
Attack Planning
Offensive Consultation
Adversarial Intelligence
Competitive Intelligence
Attack Modeling
Business Chain Vuln Assessments
Custom Physical Bypass Tool Design
Reverse Engineering
Other stuff I can’t write down…
Increasing Value Of Security Assessment Services
Traditional InfoSec
• Typical services
• Proposed value (Sales BS)
• Set up for failure
• WYSIWYG
Enhancing Services Value
• Doing services right
• Mo’ value, less money
• Eliminating failure
• Custom Delivery
New Skool InfoSec
• Red Teaming (CAST:Converged Attack Surface Tesing)
• Insider Threat Assessment
• Adversarial Modeling
• IDCa (interactive defense capability assessment)
• BCVa(business chain vulnerability analysis)
Doing the same thing and expecting different results.
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
 A vulnerability assessment is the process of identifying, quantifying,
and prioritizing (or ranking) the vulnerabilities in a system.
 http://en.wikipedia.org/wiki/Vulnerability_assessment
Reasons to Conduct
 Identify potential vulnerabilities
 Provide scoring of risk & prioritization
of remediation
 Manage environment vulnerabilities
over time to show security program
improvement, defense capability
increase and compliance with ongoing
patch, system and vulnerability
lifecycle
How it’s usually done
 Run a bunch of scanners
 Generate a report
 **Sometimes** Generate a custom
report consisting of copy/paste data
from the Vulnerability scanners and
TRY to make sure you delete the word
Nessus, qualys… and/or the previous
clients name
 Do not run “Dangerous or Experimental Checks” *instant 30%+ reduction in results
and overall accuracy*
 Do not perform Denial of Service
 Do not run thorough checks
 Do not run Web checks
 Only run ONE brand of scanner
 Limit only to known network checks
 Only scan once
Increasing Value Of Security Assessment Services
 A penetration test is a method of evaluating the security of a computer system or
network by simulating an attack from a malicious source... The process involves an
active analysis of the system for any potential vulnerabilities that may result from poor
or improper system configuration, known and/or unknown hardware or software flaws,
or operational weaknesses in process or technical countermeasures.
 http://en.wikipedia.org/wiki/Penetration_test
Increasing Value Of Security Assessment Services
Reasons to Conduct
 Identify if attackers can readily
compromise the security of the
business
 Identify potential impact to the
business
 Confirm vulnerabilities identified
 Gain a “Real World” View of an
attackers ability to “hack” the
environment and resolve issues
identified
How it’s usually done
 Do all the steps in Vulnerability
Assessment listed previously
 Run metasploit/Core/Canvas against
hosts
 Try a few other automated tools
 Call it “SECURE” If those don’t work
 Do not allow the exploitation of systems
 Restrict testing to non production systems
 Restrict the hours of testing
 Restrict the length of testing
 Improperly scope / fail to include ALL addresses
 Only perform externally
 Patch/fix BEFORE the test
 Only allow directed attacks ( no SE/ Phishing)
 Lack of focus on BUSINESS risk and increased focus on technical issue
Increasing Value Of Security Assessment Services
The IT risk management is the application of risk management to
Information technology context in order to manage IT risk.
Information security risk assessment is the process used to identify and
understand risks to the confidentiality, integrity, and availability of
information and information systems. In its simplest form, a risk
assessment consists of the identification and valuation of assets and an
analysis of those assets in relation to potential threats and vulnerabilities,
resulting in a ranking of risks to mitigate. The resulting information should
be used to develop strategies to mitigate those risks.
http://laresconsulting.com/risk.php
Increasing Value Of Security Assessment Services
Reasons to Conduct
 Compliance with regulations
 Overall health check of the InfoSec
program
 Gain understanding of program
Effectiveness
 Baseline discovery
 To show 3rd parties and customers
they are “Secure”
How it’s usually done
 Whip out a checklist
 Check stuff off on checklist
 Have a TON of interviews
 Believe every word
 Do a tick mark legend and ask people
to provide “evidence” *which is usually
faked*
 Only assess controls that are in scope
of THAT specific assessment *often
information centric*
 Do not allow ACTUAL/TECHNICAL testing and validation
 Rely on all information provided as TRUE
 Minimize scope to only include assets and controls that are part of the selected
compliance regulation and NOT the ENTIRE BUSINESS
 Allow for “Compensating Controls” to be an answer to most issues
 Expect to become compliant through outsourcing
 Expect to become compliant through product purchase/implementation
 Be unprepared
 LIE
Stop cutting off your own fingers
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
TESTING
 Skip it!
 Do It yourself
 Use Scanners to identify Vulns
 Figure out a process to track them over
time
 Manage the reduction of Vulns over time
 Manage the MTTP ( Mean Time To
Patch)
 Do the rest and make your testers
WORK hard.
DON’T RUSH IT
PLAN FOR INTERACTION
ALWAYS “Ride Along”
Connect to the REAL impact (shells don’t matter)
GO FULL SCOPE
Don’t use firms that have “SECRET” processes or can not
explain every step of the test and HOW they do it
Attack like AN ATTACKER not like a script kiddie
Use a repeatable methodology
IF THE TESTING TIME LOOKS LIKE THIS, GET A NEW TESTER
Recon Scan Enumerate Exploit
Post-
Exploit
Write
Report
1 • Pre-Engagement
2 • Intelligence Gathering
3 • Threat Modelling
4 • Vulnerability Analysis
5 • Exploitation
6 • Post-Exploitation
7 • Reporting
WWW.PENTEST-
STANDARD.ORG
HTTP://WWW.PENTEST-
STANDARD.ORG/INDEX.P
HP/PTES_TECHNICAL_GUI
DELINES
Common misconceptions
We will get owned, what's
the point
It will offend our users
Doesn’t provide enough
value
How it’s usually done
Send a 419 scam style
email
Track clicks
Write a report to show who
clicked
How it SHOULD be
done to generate
MAX value
 MAKE IT BUSINESS FOCUSED NOT IT FOCUSED
 Use multiple standards
 Remove silo’s and scope restrictions
 TEST, TEST, TEST (PBC docs ARE NOT SUFFICENT)
 A sample set does not show the ability to secure. I crack in certain parts of the
defense chain allow for the compromise of the ENTIRE COMPANY
 ALWAYS interview each and every executive to understand THEIR concerns and build
the solutions to address THEM and not always “just for the audit”
 Discuss the VALUE of systems in relevance to the business and re-weight scores
 NEVER allow a compensating control on a BUSINESS critical system. EVER
THIS is what the BIG BOYS do, catch up.
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
Increasing Value Of Security Assessment Services
The term originated within the military to describe a team whose purpose is to penetrate
security of "friendly" installations, and thus test their security measures. The members
are professionals who install evidence of their success, e.g. leave cardboard signs
saying "bomb" in critical defense installations, hand-lettered notes saying that “your
codebooks have been stolen" (they usually have not been) inside safes, etc.
Sometimes, after a successful penetration, a high-ranking security person will show up
later for a "security review," and "find" the evidence. Afterward, the term became
popular in the computer industry, where the security of computer systems is often tested
by tiger teams.
How do you know you can put up a fight if you have never
taken a punch?
Electronic
• Network Pentesting
• Surveillance/ plants
Social
• In Person Social
Engineering
• Phone Conversation
• Social Profiling
Physical
• Lockpicking
• Direct Attack
EP Convergance
• Attacks on physical systems
that are network enabled
ES Convergance
• Blackmail
• Phishing
• Profiling
• Creating moles
PS Convergance
• Tailgaiting
• Impersonation
RED
TEAM
Reasons to Conduct
 Real world test to see how you will hold up against a highly skilled, motivated and funded
attacker
 The only type of testing that will cover a fully converged attack surface
 Impact assessment is IMMEDIATE and built to show a maximum damage event
 This IS the FULL DR test of an InfoSec Program
Increasing Value Of Security Assessment Services
Reasons to Conduct
 Exercises in evaluating WHO your top5 most likely attackers are
 Full OSINT profiling on the Attackers and their capabilities
 Scenarios which are highly focused at Detecting, Confirming, Mitigating and Resolving
attacks that are the MOST likely to happen
 Testers are forced to use the capabilities of the likely attackers and train the team how to
be cool under fire
 The most relevant attacks are dealt with FIRST, you are not defending against the
pentester… you are prepping to the battle that WILL happen
Increasing Value Of Security Assessment Services
What is it?
 Evaluate threat and risk from
employee/staff/contractor/executive/etc..
 Use company provisioned asset/standard access model (limited
priv’s)
 Identify what data/assets can be accessed through authorized
channels
 Identify elevation of privilege scenarios (exploit AND non-exploit
methods)
Why do it?
 Provides visibility into “what could happen”
 A user WILL be compromised at some point
 Evaluate security posture of corporate asset
 External testing doesn’t always provide accurate measurement of
internal sourced threats
 Identify insecure internal communication channels
 Evaluate covert channel resistance/prevention
 External assessments usually only measure (1) of these (if you’re lucky)
 Measure defense capabilities internally (beyond perimeter)
 System to system communication
 Level of “noise” detection
 Data leakage/exfil abilities
 Log/data correlation
 Incident response/forensics team’s level of knowledge/expertise
Increasing Value Of Security Assessment Services
Reasons to Conduct
 Targeted at working BOTH sides of the test
 Active analysis on defense capability and impreovements / feedback can be real time
 Direct understanding of where process,policy and procedure break down in a REAL LIFE
EVENT
 Identification of Defensive Technology effectiveness
Increasing Value Of Security Assessment Services
Reasons to Conduct
 Targeted at working on identifying BUSINESS vulns
 How much can/do partners hurt you
 Where can you better defend against Partners and 3rd parties
 Who what where when and why…. Of how the business works and how it can be
materially effected by relationships
Cnickerson@laresconsulting.com
WWW.LARES.COM

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Increasing Value Of Security Assessment Services

  • 1. Of security testing and assessment
  • 17. Pain in the arse Loudmouth Hacker Punk Tells lies (professionally) Is called all sorts of bad words.. That I will likely say throughout this talk Cant code well Talks $hit Drinks a LOT Is an overall J3rk
  • 24. LARES
  • 31. OSINT SIGINT TSCM/ Bug Sweeping Exploit Development Tool Creation Attack Planning Offensive Consultation Adversarial Intelligence Competitive Intelligence Attack Modeling Business Chain Vuln Assessments Custom Physical Bypass Tool Design Reverse Engineering Other stuff I can’t write down…
  • 33. Traditional InfoSec • Typical services • Proposed value (Sales BS) • Set up for failure • WYSIWYG Enhancing Services Value • Doing services right • Mo’ value, less money • Eliminating failure • Custom Delivery New Skool InfoSec • Red Teaming (CAST:Converged Attack Surface Tesing) • Insider Threat Assessment • Adversarial Modeling • IDCa (interactive defense capability assessment) • BCVa(business chain vulnerability analysis)
  • 34. Doing the same thing and expecting different results.
  • 37.  A vulnerability assessment is the process of identifying, quantifying, and prioritizing (or ranking) the vulnerabilities in a system.  http://en.wikipedia.org/wiki/Vulnerability_assessment
  • 38. Reasons to Conduct  Identify potential vulnerabilities  Provide scoring of risk & prioritization of remediation  Manage environment vulnerabilities over time to show security program improvement, defense capability increase and compliance with ongoing patch, system and vulnerability lifecycle How it’s usually done  Run a bunch of scanners  Generate a report  **Sometimes** Generate a custom report consisting of copy/paste data from the Vulnerability scanners and TRY to make sure you delete the word Nessus, qualys… and/or the previous clients name
  • 39.  Do not run “Dangerous or Experimental Checks” *instant 30%+ reduction in results and overall accuracy*  Do not perform Denial of Service  Do not run thorough checks  Do not run Web checks  Only run ONE brand of scanner  Limit only to known network checks  Only scan once
  • 41.  A penetration test is a method of evaluating the security of a computer system or network by simulating an attack from a malicious source... The process involves an active analysis of the system for any potential vulnerabilities that may result from poor or improper system configuration, known and/or unknown hardware or software flaws, or operational weaknesses in process or technical countermeasures.  http://en.wikipedia.org/wiki/Penetration_test
  • 43. Reasons to Conduct  Identify if attackers can readily compromise the security of the business  Identify potential impact to the business  Confirm vulnerabilities identified  Gain a “Real World” View of an attackers ability to “hack” the environment and resolve issues identified How it’s usually done  Do all the steps in Vulnerability Assessment listed previously  Run metasploit/Core/Canvas against hosts  Try a few other automated tools  Call it “SECURE” If those don’t work
  • 44.  Do not allow the exploitation of systems  Restrict testing to non production systems  Restrict the hours of testing  Restrict the length of testing  Improperly scope / fail to include ALL addresses  Only perform externally  Patch/fix BEFORE the test  Only allow directed attacks ( no SE/ Phishing)  Lack of focus on BUSINESS risk and increased focus on technical issue
  • 46. The IT risk management is the application of risk management to Information technology context in order to manage IT risk. Information security risk assessment is the process used to identify and understand risks to the confidentiality, integrity, and availability of information and information systems. In its simplest form, a risk assessment consists of the identification and valuation of assets and an analysis of those assets in relation to potential threats and vulnerabilities, resulting in a ranking of risks to mitigate. The resulting information should be used to develop strategies to mitigate those risks. http://laresconsulting.com/risk.php
  • 48. Reasons to Conduct  Compliance with regulations  Overall health check of the InfoSec program  Gain understanding of program Effectiveness  Baseline discovery  To show 3rd parties and customers they are “Secure” How it’s usually done  Whip out a checklist  Check stuff off on checklist  Have a TON of interviews  Believe every word  Do a tick mark legend and ask people to provide “evidence” *which is usually faked*  Only assess controls that are in scope of THAT specific assessment *often information centric*
  • 49.  Do not allow ACTUAL/TECHNICAL testing and validation  Rely on all information provided as TRUE  Minimize scope to only include assets and controls that are part of the selected compliance regulation and NOT the ENTIRE BUSINESS  Allow for “Compensating Controls” to be an answer to most issues  Expect to become compliant through outsourcing  Expect to become compliant through product purchase/implementation  Be unprepared  LIE
  • 50. Stop cutting off your own fingers
  • 55.  Skip it!  Do It yourself  Use Scanners to identify Vulns  Figure out a process to track them over time  Manage the reduction of Vulns over time  Manage the MTTP ( Mean Time To Patch)  Do the rest and make your testers WORK hard.
  • 56. DON’T RUSH IT PLAN FOR INTERACTION ALWAYS “Ride Along” Connect to the REAL impact (shells don’t matter) GO FULL SCOPE Don’t use firms that have “SECRET” processes or can not explain every step of the test and HOW they do it Attack like AN ATTACKER not like a script kiddie Use a repeatable methodology
  • 57. IF THE TESTING TIME LOOKS LIKE THIS, GET A NEW TESTER Recon Scan Enumerate Exploit Post- Exploit Write Report
  • 58. 1 • Pre-Engagement 2 • Intelligence Gathering 3 • Threat Modelling 4 • Vulnerability Analysis 5 • Exploitation 6 • Post-Exploitation 7 • Reporting
  • 60. Common misconceptions We will get owned, what's the point It will offend our users Doesn’t provide enough value How it’s usually done Send a 419 scam style email Track clicks Write a report to show who clicked
  • 61. How it SHOULD be done to generate MAX value
  • 62.  MAKE IT BUSINESS FOCUSED NOT IT FOCUSED  Use multiple standards  Remove silo’s and scope restrictions  TEST, TEST, TEST (PBC docs ARE NOT SUFFICENT)  A sample set does not show the ability to secure. I crack in certain parts of the defense chain allow for the compromise of the ENTIRE COMPANY  ALWAYS interview each and every executive to understand THEIR concerns and build the solutions to address THEM and not always “just for the audit”  Discuss the VALUE of systems in relevance to the business and re-weight scores  NEVER allow a compensating control on a BUSINESS critical system. EVER
  • 63. THIS is what the BIG BOYS do, catch up.
  • 68. The term originated within the military to describe a team whose purpose is to penetrate security of "friendly" installations, and thus test their security measures. The members are professionals who install evidence of their success, e.g. leave cardboard signs saying "bomb" in critical defense installations, hand-lettered notes saying that “your codebooks have been stolen" (they usually have not been) inside safes, etc. Sometimes, after a successful penetration, a high-ranking security person will show up later for a "security review," and "find" the evidence. Afterward, the term became popular in the computer industry, where the security of computer systems is often tested by tiger teams. How do you know you can put up a fight if you have never taken a punch?
  • 69. Electronic • Network Pentesting • Surveillance/ plants Social • In Person Social Engineering • Phone Conversation • Social Profiling Physical • Lockpicking • Direct Attack EP Convergance • Attacks on physical systems that are network enabled ES Convergance • Blackmail • Phishing • Profiling • Creating moles PS Convergance • Tailgaiting • Impersonation RED TEAM
  • 70. Reasons to Conduct  Real world test to see how you will hold up against a highly skilled, motivated and funded attacker  The only type of testing that will cover a fully converged attack surface  Impact assessment is IMMEDIATE and built to show a maximum damage event  This IS the FULL DR test of an InfoSec Program
  • 72. Reasons to Conduct  Exercises in evaluating WHO your top5 most likely attackers are  Full OSINT profiling on the Attackers and their capabilities  Scenarios which are highly focused at Detecting, Confirming, Mitigating and Resolving attacks that are the MOST likely to happen  Testers are forced to use the capabilities of the likely attackers and train the team how to be cool under fire  The most relevant attacks are dealt with FIRST, you are not defending against the pentester… you are prepping to the battle that WILL happen
  • 74. What is it?  Evaluate threat and risk from employee/staff/contractor/executive/etc..  Use company provisioned asset/standard access model (limited priv’s)  Identify what data/assets can be accessed through authorized channels  Identify elevation of privilege scenarios (exploit AND non-exploit methods)
  • 75. Why do it?  Provides visibility into “what could happen”  A user WILL be compromised at some point  Evaluate security posture of corporate asset  External testing doesn’t always provide accurate measurement of internal sourced threats  Identify insecure internal communication channels  Evaluate covert channel resistance/prevention  External assessments usually only measure (1) of these (if you’re lucky)  Measure defense capabilities internally (beyond perimeter)  System to system communication  Level of “noise” detection  Data leakage/exfil abilities  Log/data correlation  Incident response/forensics team’s level of knowledge/expertise
  • 77. Reasons to Conduct  Targeted at working BOTH sides of the test  Active analysis on defense capability and impreovements / feedback can be real time  Direct understanding of where process,policy and procedure break down in a REAL LIFE EVENT  Identification of Defensive Technology effectiveness
  • 79. Reasons to Conduct  Targeted at working on identifying BUSINESS vulns  How much can/do partners hurt you  Where can you better defend against Partners and 3rd parties  Who what where when and why…. Of how the business works and how it can be materially effected by relationships

Editor's Notes

  • #5: Sorry ya had to wake up early
  • #6: And sit there to pay atteention
  • #7: To my stupid ppt
  • #9: Got drunk last night
  • #10: Will try not to puke while I am on stage
  • #11: Ps.. I swear…deal with it
  • #25: Who we are
  • #26: Code review
  • #27: Incident response
  • #28: Risk Assessment
  • #29: Physical security
  • #30: PenTesting
  • #31: Red Teaming
  • #55: Mike Tyson : Prophet of Infosec “ Everyone has a plan until they get punched in the face”
  • #59: I think people may THINK they do ll this and not understand how in depth we go without showing them
  • #70: Converged attacking