Assessment Methodology


In recent times, both government and private organizations have taken up cyber security as a strategic priority. Cyber criminals have often made government and private organizations their soft targets by using different attacking vectors. Unfortunately, due to lack of efficient policies, standards and complexity of information system, cyber criminals have large number of targets and they are becoming successful in exploiting the system and stealing information too.

Penetration testing is one strategy that can be used to mitigate the risks of cyberattacks. The success of penetration testing depends upon an efficient & consistent assessment methodology.

We have a variety of assessment methodologies related to penetration testing. The benefit of using a methodology is that it allows assessors to evaluate an environment consistently. Following are a few important methodologies −

  • Open Source Security Testing Methodology Manual (OSSTMM)

  • Open Web Application Security Project (OWASP)

  • National Institute of Standards and Technology (NIST)

  • Penetration Testing Execution Standard (PTES)

What is PTES?

PTES, penetration testing execution standard, as the name implies is an assessment methodology for penetration testing. It covers everything related to a penetration test. We have a number of technical guidelines, within PTES, related to different environments that an assessor may encounter. This is the biggest advantage of using PTES by new assessors because technical guidelines have the suggestions for addressing and evaluating environment within industry standard tools.

In the following section, we will learn about the different phases of PTES.

Seven Phases of PTES

The penetration testing execution standard (PTES) consists of seven phases. These phases cover everything related to a penetration test - from the initial communication and reasoning behind a pentest, through the intelligence gathering and threat modeling phases where testers are working behind the scenes. This leads to a better understanding of the tested organization, through vulnerability research, exploitation and post exploitation. Here, the technical security expertise of the testers is critically combined with the business understanding of the engagement, and finally to the reporting, which captures the entire process, in a manner that makes sense to the customer and provides the most value to it.

We will learn about the seven phases of PTES in our subsequent sections −

Pre-engagement Interactions Phase

This is the first and very important phase of PTES. The main aim of this phase is to explain the tools and techniques available, which help in a successful pre-engagement step of a penetration test. Any mistake while implementing this phase can have a significant impact on the rest of the assessment. This phase comprises of the following −

Request for an assessment

The very first part with which this phase starts is the creation of a request for an assessment by the organization. A Request for Proposal (RFP) document having the details about the environment, kind of assessment required and the expectations of the organization is provided to the assessors.


Now, based on the RFP document, multiple assessment firms or individual Limited Liability Corporations (LLCs) will bid and the party, the bid of which matches the work requested, price and some other specific parameters will win.

Signing of Engagement Letter (EL)

Now, the organization and the party, who won the bid, will sign a contract of Engagement Letter (EL). The letter will have the statement of work (SOW) and the final product.

Scoping Meeting

Once the EL is signed, fine-tuning of the scope can begin. Such meetings help an organization and the party to fine-tune a particular scope. The main goal of scoping meeting is to discuss what will be tested.

Handling of scope creep

Scope creep is something where the client may try to add on or extend the promised level of work to get more than it may have promised to pay for. That is why the modifications to original scope should be carefully considered due to time and resources. It must also be completed in some documented form such as email, signed document or authorized letter etc.


During initial communications with the customer, there are several questions that the client will have to answer for proper estimation of the engagement scope. These questions are designed to provide a better understanding of what the client is looking to gain out of the penetration test; why the client is looking to have a penetration test performed against their environment; and, whether or not they want certain types of tests performed during the penetration test.

Way to conduct test

The last part of the pre-engagement phase is to decide the procedure to conduct the test. There are various testing strategies like White Box, Black Box, Grey Box, Double-blind testing to choose from.

Following are a few examples of assessments that may be requested −

  • Network penetration test
  • Web application penetration test
  • Wireless network penetration test
  • Physical penetration test
  • Social engineering
  • Phishing
  • Voice Over Internet Protocol(VOIP)
  • Internal network
  • External network

Intelligence Gathering Phase

Intelligence gathering, the second phase of PTES, is where we perform the preliminary surveying against a target to gather as much information as possible to be utilized when penetrating the target during the vulnerability assessment and exploitation phases. It helps organizations in determining the external exposure by assessment team. We can divide information gathering in the following three levels −

Level 1 Information Gathering

Automated tools can obtain this level of information almost entirely. Level 1 information gathering effort should be appropriate to meet the compliance requirement.

Level 2 Information Gathering

This level of information can be obtained by using automated tools from level 1 along with some manual analysis. This level needs a good understanding of the business, including information such as physical location, business relationship, organization chart, etc. Level 2 information gathering effort should be appropriate to meet the compliance requirement along with other needs such as long-term security strategy, acquiring smaller manufacturers, etc.

Level 3 Information Gathering

This level of information gathering is used in the most advanced penetration test. All the information from level 1 and level 2 along with lots of manual analysis is required for level 3 information gathering.

Threat Modeling Phase

This is the third phase of PTES. Threat modeling approach is required for correct execution of penetration testing. Threat modeling can be used as part of a penetration test or it may may face based on a number of factors. In case we are using threat modeling as part of penetration test, then the information gathered in the second phase would be rolled back into the first phase.

The following steps constitute the threat-modelling phase −

  • Gather necessary and relevant information.

  • Need to identify and categorize primary & secondary assets.

  • Need to identify and categorize threats & threat communities.

  • Need to map threat communities against primary & secondary assets.

Threat Communities & Agents

The following table lists down the relevant threat communities and agents along with their location in the organization −

Location Internal External
Threat agents/communities Employees Business Partners
Management persons Contractors
Administrators(Network, System) Competitors
Engineers Suppliers
Technicians Nation States
General user community Hackers

While doing threat-modeling assessment, we need to remember that the location of threats can be internal. It takes only a single phishing e-mail or one annoyed employee who is keeping the security of organization at stake by broadcasting credentials.

Vulnerability Analysis Phase

This is the fourth phase of PTES in which the assessor will identify the feasible targets for further testing. In the first three phases of PTES, only the details about organization have been extracted and the assessor has not touched any resources for testing. It is the most time consuming phase of PTES.

The following stages constitute Vulnerability Analysis −

Vulnerability testing

It may be defined as the process of discovering flaws such as misconfiguration and insecure application designs in the systems and applications of host and services. The tester must properly scope the testing and desired outcome before conducting vulnerability analysis. The vulnerability testing can be of the following types −

  • Active testing
  • Passive testing

We will discuss the two types in detail in our subsequent sections.

Active testing

It involves direct interaction with the component being tested for security vulnerabilities. The components can be at low level such as the TCP stack on a network device or at high level such as the web based interface. Active testing can be done in the following two ways −

Automated active testing

It utilizes the software to interact with a target, examine responses and determine based on these responses whether a vulnerability in the component is present or not. The importance of automated active testing in comparison with manual active testing can be realized from the fact that if there are thousands of TCP ports on a system and we need to connect all of them manually for testing, it would take considerably huge amount of time. However, doing it with automated tools can reduce lots of time and labor requirements. Network vulnerability scan, port scan, banner grabbing, web application scan can be done with the help of automated active testing tools.

Manual active testing

Manual effective testing is more effective when compared to automated active testing. The margin of error always exists with automated process or technology. That is why it is always recommended to execute manual direct connections to each protocol or service available on a target system to validate the result of automated testing.

Passive testing

Passive testing does not involve direct interaction with the component. It can be implemented with the help of the following two techniques −

Metadata Analysis

This technique involves looking at the data that describes the file rather than the data of the file itself. For example, the MS word file has the metadata in terms of its author name, company name, date & time when the document was last modified and saved. There would be a security issue if an attacker can get passive access to metadata.

Traffic Monitoring

It may be defined as the technique for connecting to an internal network and capturing data for offline analysis. It is mainly used to capture the “leaking of data” onto a switched network.


After vulnerability testing, validation of the findings is very necessary. It can be done with the help of the following techniques −

Correlation between tools

If an assessor is doing vulnerability testing with multiple automated tools then for validating the findings, it is very necessary to have a correlation between these tools. The findings can become complicated if there is no such kind of correlation between tools. It can be broken down into specific correlation of items and categorical correlation of items.

Protocol specific validation

Validation can be done with the help of protocols also. VPN, Citrix, DNS, Web, mail server can be used to validate the findings.


After the finding and validation of vulnerability in a system, it is essential to determine the accuracy of the identification of the issue and to research the potential exploitability of the vulnerability within the scope of the penetration test. Research can be done publicly or privately. While doing public research, vulnerability database and vendor advisories can be used to verify the accuracy of a reported issue. On the other hand, while doing private research, a replica environment can be set and techniques like fuzzing or testing configurations can be applied to verify the accuracy of a reported issue.

Exploitation Phase

This is the fifth phase of PTES. This phase focuses on gaining access to the system or resource by bypassing security restrictions. In this phase, all the work done by previous phases leads to gaining access of the system. There are some common terms as follows used for gaining access to the system −

  • Popped
  • Shelled
  • Cracked
  • Exploited

The logging in system, in exploitation phase, can be done with the help of code, remote exploit, creation of exploit, bypassing antivirus or it can be as simple as logging via weak credentials. After getting the access, i.e., after identifying the main entry point, the assessor must focus on identifying high value target assets. If the vulnerability analysis phase was properly completed, a high value target list should have been complied. Ultimately, the attack vector should take into consideration the success probability and highest impact on the organization.

Post Exploitation Phase

This is the sixth phase of PTES. An assessor undertakes the following activities in this phase −

Infrastructure analysis

The analysis of the entire infrastructure used during penetration testing is done in this phase. For example, analysis of network or network configuration can be done with the help of interfaces, routing, DNS servers, Cached DNS entries, proxy servers, etc.


It may be defined as obtaining the information from targeted hosts. This information is relevant to the goals defined in the pre-assessment phase. This information can be obtained from installed programs, specific servers like database servers, printer, etc. on the system.

Data exfiltration

Under this activity, assessor is required to do mapping and testing of all possible exfiltration paths so that control strength measuring, i.e., detecting and blocking sensitive information from organization, can be undertaken.

Creating persistence

This activity includes installation of backdoor that requires authentication, rebooting of backdoors when required and creation of alternate accounts with complex passwords.


As the name suggest, this process covers the requirements for cleaning up system once the penetration test completes. This activity includes the return to original values system settings, application configuration parameters, and the removing of all the backdoor installed and any user accounts created.


This is the final and most important phase of PTES. Here, the client pays on the basis of final report after completion of the penetration test. The report basically is a mirror of the findings done by the assessor about the system. Following are the essential parts of a good report −

Executive summary

This is a report that communicates to the reader about the specific goals of the penetration test and the high level findings of the testing exercise. The intended audience can be a member of advisory board of chief suite.


The report must contain a storyline, which will explain what was done during the engagement, the actual security findings or weaknesses and the positive controls that the organization has established.

Proof of concept/technical report

Proof of concept or technical report must consist the technical details of the test and all the aspects/components agreed upon as key success indicators within the pre engagement exercise. The technical report section will describe in detail the scope, information, attack path, impact and remediation suggestions of the test.