Penetration Testing Checklist: Process, Tools & Techniques

Penetration testing checklist feature

Roy Golombick

May 21, 2024

A penetration test (or pen test) is a simulated cyberattack against an application, system, or network to identify vulnerabilities that can be exploited by real hackers. It is conducted by a team of offensive cybersecurity professionals (red teamers) who will use methods and tools that mimic the actions of potential attackers to comprehensively evaluate the security robustness of the target environment.
This comprehensive penetration testing checklist serves as an invaluable resource to ensure that you have covered all essential aspects when conducting a penetration test. By following this checklist, you can methodically verify that your testing process is complete, effective, and aligned with industry best practices.

Popular Types of Penetration Tests

  • External Testing: Targeting assets that are visible on the internet, such as websites and external-facing servers.
  • Internal Testing: Simulating an internal threat to see how much damage a disgruntled employee could cause.
  • Web Application Testing: Identifying security vulnerabilities in web applications and their components, such as APIs, front-end servers, and back-end systems. 
  • Wireless Testing: Evaluating the security of an organization’s wireless local area network (WLAN) and related wireless protocols such as Bluetooth, ZigBee, and Z-Wave.
  • Mobile Application Testing: Identifying vulnerabilities in mobile apps running on devices like smartphones and tablets.

To maximize the benefits of a pen test, the client organization and the testing team must agree on a set of rules known as the “Rules of Engagement.” These rules outline the scope of the test, the methods to be used, the timeframe, and other critical parameters to ensure the test is conducted safely, ethically, and legally. 

The entire penetration testing process, from planning to final report, is carried out in several stages.

Why Conduct a Penetration Test?

1. Identify and Prioritize Security Vulnerabilities: Penetration tests help uncover exploitable vulnerabilities in your systems before attackers can find and exploit them. This proactive approach allows you to understand the weaknesses in your security posture and take corrective actions.

2. Validate the Effectiveness of Security Measures: Through penetration testing, organizations can validate the strength of their defensive mechanisms and end-user adherence to security policies. This helps ensure that security measures are functioning as intended and are capable of defending against current hacking techniques.

3. Regulatory Compliance: Many industries are governed by regulatory requirements that mandate regular security assessments, including penetration testing. Compliance with standards such as PCI DSS, HIPAA, or GDPR not only avoids legal and financial repercussions but also protects sensitive data.

4. Avoid Costly Breaches: The cost of a security breach reached $4.45 million according to  IBM’s Cost of a Data Breach Report 2023. On top of that, data breaches cause reputational damage, and operational downtime. Penetration testing is a cost-effective way to reduce the risk of breaches by identifying and mitigating vulnerabilities early.

5. Enhance Cyber Incident Response: Pen tests simulate real-life cyberattacks and provide a unique opportunity for security teams to test their incident response capabilities. This experience is invaluable when dealing with actual security incidents.

When to Conduct a Penetration Test?

1. After Significant Changes: Any significant change in your network, such as the deployment of new network infrastructure, software updates, or the addition of new applications, should prompt a penetration test to ensure that no new vulnerabilities have been introduced.

2. Regularly Scheduled Intervals: Depending on the size and complexity of your environment, as well as industry best practices, penetration tests should be conducted at least annually. More frequent tests may be necessary for industries facing higher security risks or those that store sensitive information.

3. In Response to New Threats: When new types of cyberattacks or vulnerabilities (like zero-days) are reported, it’s wise to conduct targeted penetration testing to ensure that your systems are not susceptible to these new threats.

4. Compliance Requirements: Often, regulatory standards will dictate how often you need to perform penetration testing. Adhering to these guidelines not only keeps you compliant but also ensures consistent security assessments.

5. Prior to Launch of New Services: Before going live with new services or applications, conducting a penetration test ensures that any potential security issues are addressed pre-launch, safeguarding both the service and its users from day one.

The 5 Stages of a Penetration Test

  1. Reconnaissance

In the first stage of a penetration test, the client organization provides the penetration tester with essential information about their systems, which may include network diagrams, IP address ranges, types of operating systems used, and details about web applications. This provided information forms the baseline for initial reconnaissance efforts.

Depending on how much information the client gives the testing team, there are three types of pen tests:

  • Black Box Testing: The testing team has no prior knowledge of the target system, simulating an external attack by an outsider without insider information.
  • White Box Testing: The testers are provided with full disclosure of the environment, including network maps and credentials, resembling an in-depth audit from an internal perspective.
  • Grey Box Testing: This approach offers partial knowledge about the system, combining elements of both black and white box testing to simulate an attack by someone with limited insider access.

The penetration testers also engage in independent information gathering to supplement what the client has provided. This involves a mix of passive and active reconnaissance techniques. 

Passive reconnaissance might include searching public records or websites, analyzing social media, and gathering data from third-party data leaks without directly interacting with the target systems. 

Active reconnaissance involves more direct interaction with the target system but is conducted carefully to avoid any disruption. 

  1. Scanning

Once all necessary information is gathered, it’s time for the scanning phase. Here, the penetration tester tries to look for vulnerabilities within the target using a variety of tools and techniques. Scanning includes using automated scanning software to identify open ports, live systems, services running on servers, and vulnerabilities associated with them. 

Recently, numerous cybersecurity service providers have begun to label their services as “penetration testing,” when in fact they are only conducting basic vulnerability scans. As a client, it’s important to recognize the distinction, and that scanning is only a part of the broader penetration testing process.

  1. Vulnerability Assessment

In this phase, the penetration tester uses the data gathered in the previous two stages to identify vulnerabilities and determine if and how they can be exploited. Like scanning, vulnerability assessment tools can be used individually, but they’re much more powerful when combined with the other penetration testing phases.

There are many resources for vulnerability assessment, such as the National Vulnerability Database (NVD). NVD is maintained by the U.S. government, and contains valuable data on known vulnerabilities that have been cataloged and classified. It provides detailed descriptions, severity ratings based on CVSS scores, and references to help organizations understand and address the vulnerabilities relevant to their systems.

  1. Exploitation

This is where the penetration test really kicks into gear. During the exploitation phase, the penetration tester actively attempts to exploit the vulnerabilities identified in the previous stages. This involves using a variety of techniques and tools to gain unauthorized access to systems, escalate privileges, or execute malicious actions within the environment. The objective is to demonstrate how an attacker could leverage these vulnerabilities to compromise the system’s security.

Exploiting vulnerabilities and bypassing security controls takes a great bit of skill, and must be done with caution as to not damage or crash the target system.

  1. Reporting

Producing a final report is the last step in the penetration testing process. The report consolidates all the findings from the test, including the vulnerabilities detected, the exploits attempted, and the potential impact on the system. It provides a comprehensive analysis of the security posture of the target environment, offering detailed recommendations for remediation to address identified vulnerabilities and strengthen defenses.

The report should be clear, structured, and accessible to various stakeholders, including technical teams and executive management, ensuring that all relevant parties understand the risks and the steps needed to mitigate them. It typically includes: 

  • An executive summary
  • Detailed technical findings
  • Supporting evidence such as screenshots and logs
  • A prioritized list of recommendations based on the severity and potential impact of each vulnerability.

Essential Pen-Testing Tools

Across the various stages of a penetration test, red teamers utilize a wide range of tools to probe, analyze, or exploit their target. Here are the most popular tools based on their functionality and role in the pen testing process:

OP Innovate WASP

OP Innovate WASP is a cutting-edge automated penetration testing tool that maximizes visibility into your application security posture and minimizes risk exposures with continuous expert-level penetration testing and code validation.

WASP combines continuous penetration testing with attack surface management (ASM) to enable application security professionals to constantly test, discover, assess, and manage their internal and external exposure

  • Focus: Provides a focused remediation plan based on the most impactful findings.
  • Contextual Risk Scoring: Our risk-based vulnerability scoring process assesses vulnerabilities across your attack surface by prioritizing remediation based on the risks they pose to your organization. 
  • Fast Remediation: WASP  provides a full report of your vulnerability data in a dashboard and feeds it directly into your dev workflow (JIRA etc.), dramatically reducing meantime to remediation.

Network Scanning

  • Nmap: A versatile network scanning tool that uses raw IP packets to determine what hosts are available on the network, which services they’re running, and their operating system.
  • Wireshark: A network protocol analyzer that captures packets in real time and displays them in human-readable format for troubleshooting, analysis, and software and protocol development.
  • Aircrack-ng: A suite of tools for 802.11 wireless network security auditing, primarily known for its ability to crack WEP and WPA/WPA2 PSK keys.

Vulnerability Scanning

  • Nessus: An industry-leading vulnerability scanner that conducts automatic scans to identify vulnerabilities, malware, and compliance issues with detailed remediation guidance.
  • OpenVAS: A comprehensive vulnerability management solution consisting of various components, including a scanner, a manager, and a collection of network vulnerability tests.

Social Engineering

  • Social Engineer Toolkit (SET): An open-source penetration testing framework for social engineering. It consists of several attack vectors that allow you to create and simulate an attack quickly. 

Password Cracking

  • John the Ripper: Fast password cracking tool supporting numerous algorithms, useful for detecting weak Unix passwords.
  • Hashcat: Advanced password recovery tool, known for its speed and versatility, capable of handling a myriad of hash types and encryption algorithms.

Exploitation Frameworks

  • Metasploit: The world’s most popular penetration testing framework. It consists of various tools you can use to test vulnerabilities, execute attacks, and escalate privileges.

OP Innovate’s Penetration Testing as a Service (PTaaS)

IP Innovate sits at the forefront of pioneering cybersecurity solutions. As such, we introduced WASP – an all-encompassing cybersecurity platform. 

We combine routine pen test sprints run by our CREST-certified offensive security team with our innovative WASP platform, offering continuous scanning and reconnaissance. Our hybrid Penetration Testing as a Service (PTaaS) approach offers the best of both worlds, leveraging the efficiency of automation while harnessing the expertise of human testers.
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