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Instructor: There are many different types
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of penetration tests and assessments,
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including goals-based, objectives-based, compliance-based,
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pre-merger, supply chain, and red team assessments.
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A goals-based assessment
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is designed with a specific goal in mind.
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In this case, the penetration tester
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may attempt to find as many unique ways as possible
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to achieve that specific goal,
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such as breaking into a facility
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to test its physical security.
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Now, for example, let's say a tester
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might want to come in through the front door.
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They might use social engineering
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and piggyback or tailgate in.
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They might jump over a fence
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or even pick a lock on the door.
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For a goals-based assessment,
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it really doesn't matter how they go about doing it
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as long as they're successful
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in trying to achieve that specific goal.
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In this example, gaining physical access to that facility.
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Next, we have objective-based assessments.
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Now, objective-based assessments
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are those where a tester seeks to ensure
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that the information remains secure.
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If this information is on a file server inside the facility,
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then there are many different ways to get that information.
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You could break in using physical methods
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to steal the hard drive.
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You could hack into the server using a server-side exploit.
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Or you could even use a phishing attack
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to gain access to a system
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by having the user click on a malicious link.
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Again, it really doesn't matter how we go about it
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as long as we make sure
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that the objective of the assessment is clear,
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ensuring that the information is safe from attack
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from as many sides as possible.
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For this reason, this type of testing
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is more similar to a real attack,
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because the penetration tester can be creative
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and try various methods for stealing that information.
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And really, they only have to be successful
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one time or one way
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to consider that they have met their objective.
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The third type of assessment
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is known as a compliance-based assessment,
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and this focuses on finding out if policies and regulations
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are being properly followed.
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This is one of the most common types of penetration tests
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that are conducted in our industry.
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For example, if an organization takes credit cards,
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they have to follow the rules for PCIDSS.
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All the major credit card processors
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like Visa, MasterCard, and American Express
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have all agreed to set up regulations and policies
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that require a regular scanning of a checklist of items
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if that organization is going to be allowed
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to process or store customer credit cards.
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In this type of penetration test,
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the objectives are clearly defined
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and the penetration tester can utilize a checklist
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to verify that everything is properly scanned
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and found to be secure.
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This checklist may include things like password policies,
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data isolation policies, limiting network storage access,
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key management, and so on.
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The objectives are always clearly stated
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in this type of a test.
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Other examples of compliance-based assessments
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include GDPR, HIPAA,
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Sarbanes-Oxley, and GLBA compliance audits.
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A pre-merger assessment is our fourth type of assessment.
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A pre-merger assessment is gonna be conducted
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between two companies
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before they merge with each other
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during a period of time known as due diligence.
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During this timeframe, each company is gonna look
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at the other company's financial records, personnel records,
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and often they'll require
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a third party penetration testing firm
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to assess the other company's network,
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with their permission, of course,
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in order to determine if a merger
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and the interconnection of those two networks
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could weaken the overall cybersecurity posture
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of either company.
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Another type of penetration test
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is known as a supply chain assessment.
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Now, a supply chain assessment occurs
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when a company requires its suppliers
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to ensure that they've met a given level
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of cybersecurity requirements
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before you'll do business with them.
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As a professional penetration tester,
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it's always gonna be important to be careful
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with this type of assessment
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and gain permission from both the organizations
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that are asking for the assessment
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and the one you're assessing
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prior to conducting that assessment.
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As a third party organization,
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that penetration testing company
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cannot simply start hacking an organization's supplier
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to see if they're secure.
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Instead, you must get permission
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from the owner of the network,
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which in this case would be the supplier,
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even though the person who's paying you, your client,
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might be the other organization.
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If permission is granted, however,
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and it's within the bounds of the contract
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and the statement of work,
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then the penetration tester
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should attempt to break into the supply chain
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because oftentimes the supply chain is the weakest link
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in a large enterprise or organization.
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For example, a major retailer, Target, in the United States
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actually suffered a major security breach
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of their network several years ago.
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Instead of the criminal threat actors
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going after Target's networks directly though,
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they exploited a vulnerability
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at one of Target's smaller suppliers,
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which was an air condition supply company,
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and their network security was much weaker
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but it was still interconnected
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into the more secure network owned by Target.
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Now, criminals are always gonna seek the path
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of least resistance,
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and therefore it's important to ensure
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a high cybersecurity posture
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for any organizational network you have
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and verify the trustworthiness and security
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of any of the supplier networks
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that are gonna interconnect
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into your organizational network.
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The final type of engagement we have
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is called a red team assessment,
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which is the execution of a penetration test
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against the organizational network
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by its own internal penetration testers.
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These penetration testers are also known as the red team,
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and they're gonna be authorized
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to conduct security exercises
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that are on a production network,
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a virtualized environment, or both.
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The red team are often considered the offensive side
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of the cybersecurity industry,
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while our blue team is considered the defensive side.
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If the red team is tasked with conducting the assessment
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in a virtualized environment,
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then the organization is also gonna require
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their network defenders and cybersecurity analysts
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to connect into that environment
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and participate as the defenders
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for the engagement as the blue team.
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Often, there'll also be a white team
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to oversee this engagement,
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and they act as the referee
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and ensure the red team is playing fairly
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as well as determining if the blue team
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is able to observe and stop the attacks
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that the red team is throwing.
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These engagements will serve as a form of war gaming
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that allows both the attackers and defenders
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to increase their own skill
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by conducting and observing real world attacks
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in an isolated virtual environment.
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Now, once the type of assessment is chosen,
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the team will meet
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with the client organization's stakeholders
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to determine which strategy
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they're gonna use during the engagement.
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Now, there are three common strategies that we can use.
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There is unknown environment testing,
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partially known environment testing,
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and known environment testing.
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An unknown environment test
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refers to the assessment where the penetration tester
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has no prior knowledge of the target organization
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or their network.
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This simulates an outside attack
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from the perspective of an external hacker
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and focuses solely on what an external attacker could see
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while completely ignoring an insider threat.
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This type of assessment does require more time
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and is therefore usually gonna be much more expensive
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than a partially known environment
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or a known environment assessment.
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In an unknown environment test,
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the penetration tester is gonna need to spend a lot of time
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doing information gathering and vulnerability scanning
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in order to learn all about the network
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and how to best exploit its weaknesses.
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The biggest benefit of an unknown environment test
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is that the penetration tester
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conducts the entire engagement
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as if they were an actual threat actor
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by scanning for available network resources,
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identifying live hosts, scanning for open ports,
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and fingerprinting running services
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before they actually exploit any of the assets,
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just like a real unauthorized attacker would.
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Now, a partially known environment test
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is the most common type of assessment,
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and it entails partial knowledge of the target organization
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and their information systems.
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For example the organization
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may provide the penetration tester with their IP range
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to ensure they're only probing their networks
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and not some other organization's network by mistake.
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This type of test may also be used
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to simulate an insider threat
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who has minimal knowledge of the organization,
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like a regular employee would.
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For instance, the penetration tester
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may be asked to go on site,
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they'll be given a username and password,
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and they'll be able to conduct their assessment
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from the perspective
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of an authenticated standard employee user account.
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The assessor can then see what kind of data could be taken,
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what servers are subject to privilege escalation,
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and other types of issues that are common
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to insider threats.
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A partially known environment test
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allows the penetration tester
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to decrease the amount of time spent
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in the information gathering phase,
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and therefore it allows them to spend more time
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identifying potential vulnerabilities and exploiting them.
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A potentially known environment test
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is also commonly used to test web applications and APIs
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for different security vulnerabilities
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by giving the penetration tester
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some information about the application or API,
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such as its internal functionality
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and the basic inputs and outputs,
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but not the entire source code.
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Now, the third type we have
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is called a known environment test,
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and a known environment test is an assessment
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in which the penetration tester
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is given all the details about the organization,
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the network, the systems, and the underlying architecture.
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As part of the contract,
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the assessor might be given network diagrams, IP addresses,
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versions of operating systems, and services that they use.
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We would also receive a full copy of the source code
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and associated documentation
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if we're gonna be doing a web application or API assessment.
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When conducting a known environment test,
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the penetration tester is able to spend more time
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probing for vulnerabilities and exploits
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without having to spend as much time
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in the information gathering phase,
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because all the details
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have already been provided in a truly transparent manner.
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(upbeat music)
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