Penetration Testing Getting the Most out of Your Assessment. Chris Wilkinson Crowe Horwath LLP September 22, 2010

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1 Penetration Testing Getting the Most out of Your Assessment Chris Wilkinson Crowe Horwath LLP September 22, 2010

2 Introduction Chris Wilkinson, CISSP Crowe Horwath LLP Product Manager - Penetration Testing Cell: (219) Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 2

3 Security Buzzword Bingo ( This will be fixed in the next release Let s see You design something better We re fully ISO compliant We think it is secure enough If you hadn t told anyone, it would still be secure No comment Our customers love our product It doesn t need to be secure It s a feature our users want We use cryptography We have CISSP certified engineers It would be too expensive to fix that No one has ever found any problems That s just theoretical mumbo jumbo Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 3

4 Agenda Definitions Penetration Testing Methodology The Real Value of Risk Vulnerability vs. Penetration Assessments White vs. Grey vs. Black Box Approaches to Tests Anonymous vs. Authenticated Evaluating Penetration Assessment Value Security Practice Example Other Items? Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 4

5 Pen Testing Definitions External Penetration Assessment (EPA) An attacker from their house/company/country, not located inside your network Internal Penetration Assessment (IPA) An assessment that takes place behind the firewall. Just as if someone was at their workstation inside the company walls. Internal Network Workstation Server Firewall Workstation Internet External Network Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 5

6 Penetration Testing Paradigm Let s relate the security of your network to your home External Penetration Assessment Going to focus on the External Controls available to public Windows, Doors, Structure are secured Front door acting as the firewall Internal Penetration Assessment Going to focus on the Internal Controls available to family and visitors Who do I let into my house? Where do I keep my valuables? Who has access to them and how are they secured? Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 6

7 Pen Testing Definitions Continued Service Server such as web, , etc. (ESPN) Port Communication channel on which services can talk (Channel 32) Vulnerability A weakness in a service or application. (Free HBO) Exploit Technique used to take advantage of the vulnerability to achieve inappropriate access. (Cheater Box) Exposure The resulting potential impact to the system or organization. (Lost Customer Revenue) Population Exposure The number of people that can potentially leverage the exposure for inappropriate access. (Subscriber Base) Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 7

8 Methodology Technical Assessment Layer 1 - Information Gathering Recon and Port Scans Layer 2 - Technical Assessment of Services Service list is built and confirmed EPA: Web Servers, Mail Servers, VPN Services IPA: OS Patching, Database Configuration, Password Analysis Human Layer - Social Engineering Testing Telephone Physical and Dumpster Diving Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 8

9 Question What is the difference between a penetration assessment and a vulnerability assessment? Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 9

10 Vulnerability vs. Penetration Assessments What is a Vulnerability Assessment? Lists out potential security issues. Does not take into account business impact. What is a Penetration Assessment? Elimination of False Positives Business Impact Analysis of Vulnerabilities What are they not? A 100% identification of all vulnerabilities. Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 10

11 Penetration Assessment Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 11

12 What is the Real Risk? When analysis is performed on any exposure, we must focus on the REAL risk to the infrastructure as well as the business. (This is a penetration assessment) Factors: Type of unauthorized access acquired Information (and level of sensitivity) that is accessible Additional system access Exposure population Difficulty of exploitation (often not considered) Let s look at a quick example Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 12

13 Un-Patched Machine X Questions that I must ask prior to Risk Ranking: Is exploit code publicly available? What privilege level does the exploit provide? Can I safely exploit the system? What is the purpose of the system? What information does the access allow me to obtain? How sensitive is the data? Can I gain further access into the network? (Password Reuse, Elevated Services) Are detective controls (Intrusion Detection) deployed? Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 13

14 Are Penetration Tests Always The Answer? Where is the Value? Do we have internal capabilities to translate the risk into business impact? Typically seen in larger organizations. Periodic Vulnerability Assessments are a necessity. Especially from an external perspective (Exposure Population) I left my garage door open the other night Question: What is the difference between a white, grey and black box assessment? Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 14

15 Pen Testing Approach White vs. Grey vs. Black Box Approach Descriptions: Black No Knowledge of Infrastructure Grey Limited Knowledge of Infrastructure White Collaboration with IT Department No service provider should ever perform a purely Black Box approach How much information is enough? Depends on goals of the assessment Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 15

16 White vs. Grey Approach Grey Box Benefits Testing of Incident Response Plan Testing of IDS/IPS devices* Where should they alert? EPA vs. IPA Clean Report White Box Benefits Less Layer 1 activities Efficiencies in Layer 2 More in depth coverage Targeting of specific systems Business Impact Analysis Translation of Risk Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 16

17 How do we Facilitate a Whiter Approach? Confirmation of subnets and scope early in the assessment. These activities will be performed regardless, the key is WHEN. Collaboration with IT on subnets that are sensitive in nature This can work both ways, either to test or to avoid. Use of individuals who are familiar with the infrastructure Independence is not always a good thing. Remember, assessments are typically performed with the restriction of time. Attackers do not have this constraint. The most efficient use of time is at the core of receiving value from the assessment. Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 17

18 Anonymous vs. Authenticated Usernames & Passwords Matter (User Access) The reality is user s will pick weak passwords. QUESTION: If I could only guess one password, what would I guess? Or users will open malicious s and download Trojan Horses Attackers will obtain or already have user access From an Penetration Assessment perspective: If we spend more time trying to breach layer 1, that is less time analyzing subsequent security layers (Anonymous Assessment) If we need to take an anonymous approach we must focus on obtain user access before moving forward. Attackers have all the time in the world. We do not! Therefore authenticated penetration assessments speed the process up and help to identify deeper security issues. Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 18

19 How Do I Get the Best Value? Items to consider: Can I take a collaborative effort? White Hat/Black Hat/Grey Hat Scope Do I want an exhaustive analysis? Will a sample approach suffice? Do I want to test Incident Response or detective controls within IT? Do I want to test both people & technology? Social Engineering: Who do I test? (Repeat Offenders, Various Titles, Geographic locations?) Do I want an authenticated approach? Spending less time on layer 1 allows for more analysis spent on security layer 2 and allows for better business impact analysis Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 19

20 How Do I Get the Best Value Continued Other Considerations: Current Client Base & References People Resumes Are the resources trained and up to date? Interview the resources delivering the service Obtain sample deliverables Management involvement PRICING Properly scope the assessment Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 20

21 What Can You Do Right Now? Password Management One of the most common mistakes is password reuse Attackers will often compromise: A workstation and then use the same password to access a server A local administrator account to access a domain administrator account Solution (Password Zones Local Administrator Access): Group like devices based on functionality and ensure they are configured with the same password Passwords should not be reused between groups Example: All Accounting workstations contain Password A All Human Resources workstations contain Password B All Servers acting as File Servers contain Password C Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 21

22 Questions or Comments? Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 22

23 Contact Information Chris Wilkinson, CISSP Crowe Horwath LLP Product Manager - Penetration Testing Cell: (219) Crowe Chizek and Company LLC, which is a member of Horwath Crowe Horwath LLP 23

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