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Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP [email protected] +1-410-544-3435

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Page 1: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Assessments, Audits, and Penetration Tests, Oh My

Ira Winkler, [email protected]

+1-410-544-3435

Page 2: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Why This Presentation?

Everyone wants to assess their vulnerabilties

Most people think they need a penetration test

They actually need something more basic

They don’t really know what they needThey really don’t know what their

options are

Page 3: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

More Importantly

The people performing the work don’t know the issues either

Sometimes they are doing things that are “cool”

They don’t know what their deliverables or end results should be

Sometimes they underbid and give people what they pay for, not what they wanted

Conservatively, 75% of consultants fit into this categoryMy horror story

Page 4: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

The Classification of ConsultantsDon’t know what they don’t knowKnow what they don’t knowKnow what most others don’t know

they don’t know

Page 5: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

The Critical Question to AskWhy do you want a penetration test?The answer should specify the actual workBe careful about possible disappointment

in the customerThere may be disappointment in the

testersTypically, penetration tests will not be

performed

Page 6: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

A Basic – Only Two Ways to HackThis is the core reason of any testAnyone can learn to hack a computerTake advantage of problems built into

the operating systemTake advantage of admin and user

configuration errors

Page 7: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

What are We Talking About?A Penetration Test tries to

compromise securityAn Assessment attempts to find as

many vulnerabilities as possibleAn Audit tests to a specific standardPenetration tests are generally the

least useful

Page 8: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Audits

An assessment to a specific standardSome audits are technical, some are

operational

Page 9: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Common Standards

BS7799/ISO 17799CoBITSAS70DashboardsCorporate standardsHIPAA

Page 10: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Choosing an Audit and StandardDepends on purposeISO 17799 is a regulatory requirement

in some countriesSAS70 has been widely accepted to

show other peopleDashboards developed for Six SigmaIf you don’t need a specific standard,

perform an assessment

Page 11: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Who Should Perform an AuditSince the standards are boiler plate, a

person with limited skill can run the auditThe people should be familiar with the

standardSome organizations provide certification for

the evaluatorsSAS70 requires the oversight of a CPA firmIt depends on who will look at the resultsLook for sample reports

Page 12: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

General Criteria

This should be completely overtAuditors may not have to touch

computer systemsThey should have the complete

cooperation of the organizationAudits seem almost always adversarial

Page 13: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

AssessmentsA free form attempt to locate

vulnerabilities in an organizationThere are no universal standards to followThe methodology depends on what is

agreed upon between the client and the tester

Typically companies have a standard assessment methodology

Work should be bound in advance

Page 14: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Typical Methodology

Information gatheringNetwork mappingHigh level reconnaissanceDetailed assessment where appropriateManual techniquesCreate reportBrief client

Page 15: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Method of Scans

Network scansHost scans

Page 16: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

General Notes

An assessment is completely overtThere should be complete access

granted by the administrators and full support available

Someone should be watching the assessment team at all times, if possible

Page 17: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

The Results

Identification of as many vulnerabilities as possible

The methodology should focus on thatMOST IMPORTANTLY, a prioritized

plan to address the vulnerabilitiesThe identification of problems without

solutions is generally worthless

Page 18: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Notes on Pricing

Be concerned about prices that are too cheap

Expensive prices don’t indicate qualityWatch out for ISS scanner outputWatch out for other things that look

good, but are boiler plateQuality of the people becomes more

important

Page 19: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Notes on Staffing

Assessors should be technically competent

Watch the bait and switchAsk for resumes of people who will

actually perform the work

Page 20: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Penetration Tests

Purely an attempt to compromise securityThey may find unique problems that are

not found through other assessmentsThe test should be completely covertThere should be no cooperation from the

target, within reasonThe goal is to prove that security can fail

Page 21: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Why Perform a Pen Test

To see where you are, when you don’t know

As part of a larger vulnerability assessment

To test operational readinessTo get management attention

Page 22: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Ideal Goals of a Pen Test

See how a malicious party may attack you and how far they would get

See if you can detect the attacksIdentify as many vulnerabilities as

possibleTo get the attention of management

Page 23: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Why Not Perform a Pen Test

They are the least usefulThey are the least efficientThey can cause a great deal of damageThey can cause a serious political

problemsThey require the most skill, that is

seriously scarceYou need to have a tight plan if you are

detected

Page 24: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Notes on Social Engineering

Social Engineering will make a penetration test more realistic

Tests operational and physical vulnerabilities

They require more damage controlThere is much more sensitivity as to what

and how you report thingsI strongly recommend only really trained

people perform the work

Page 25: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Types of Penetration Tests

Outsider no knowledgeOutsider with inside knowledgeLow level insiderHigh level insider (Administrators)Social Engineering

Page 26: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Critical Success Factors

Quality of the people performing the work

This is even more critical than with an assessment

Clear definition of end resultsFocus on business goals, not technical

Page 27: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Keys of the Test

Results indicate the scope of the problem from a business perspective

Damage control in effectMethods used are all commonNo inside information usedPeople were all skilled

Page 28: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

General DisclaimerRunning tools, such as CyberCop, nmap, war

dialers, etc., is not a penetration testThey may be tools of a pen test, but they are

not a pen testRules of engagement must be clearly definedI strongly recommend that someone watch the

pen test team as much as possible to protect both sides

Make sure there are recent backups33% of the time, I have discovered actual

criminal activities

Page 29: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Hiring Hackers?

The logic is, “Who better to protect the system than the people who know how to break it?”

The problem is that it is infinitely harder to protect a system than to hack it

Just because you can shoot a gun, it doesn’t mean you can design and build a bullet proof vest

The best penetration testers I have known were administrators who go into security or worked for the Government

Hire a resume, not criminal records

Page 30: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

Use the Right Test for the Right PurposesAudits only for a specific purposeAssessments when you actually want

productive resultsPenetration tests only when you really

need them

Page 31: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

General General Notes

Make sure that you save enough money to fix problems

Make sure that you get qualified people to do the work

You better get recommendations that you can actually use

Page 32: Assessments, Audits, and Penetration Tests, Oh My Ira Winkler, CISSP ira_winkler@hp.com +1-410-544-3435

For More Information

Ira Winkler, [email protected]

+1-410-544-3435