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Guide: What is Penetration Testing? | What is Pen Testing?

Guide What is Penetration Testing What is Pen Testing

Penetration Testing is a form of adversary emulation to find a successful attack path from peripheral assets to crown jewels. 

Penetration testing, also known as pen testing, is a simulated cyber attack against an organization’s computer systems, networks, or web applications. It is a proactive approach to identifying vulnerabilities and weaknesses within an organization’s security posture, allowing it to take appropriate measures to mitigate risks before malicious actors can exploit them. Pen Testing differs from vulnerability management, patch management, ASM and other similar practices in the following ways:

  1. Attacker-centric approach: Penetration testing adopts an attacker’s mindset, mimicking the tactics, techniques, and procedures (TTPs) used by real-world threat actors. This approach ensures that the testing accurately reflects the potential threats the organisation faces.
  1. Proof of exploitation: Penetration testing helps organizations demonstrate the actual impact of vulnerabilities by providing proof of exploitation. This evidence can be used to convince internal stakeholders of the urgency and importance of addressing the identified security gaps.
  1. Noise reduction and accuracy: By simulating real-world attacks, penetration testing can significantly reduce the “noise” or false positives often associated with vulnerability scanning tools. It provides a more accurate representation of the exploitable vulnerabilities, typically achieving an accuracy rate of 98% or higher.
  1. Discovery of attack paths: A key objective of penetration testing is to identify potential attack paths that could lead to the organization’s most critical assets, often referred to as “crown jewels.” This includes discovering vulnerabilities and entry points from both external (internet-facing) and internal (within the organization’s network) perspectives.

What is Continuous Pen Testing & its Impact on CISO?

Continuous Penetration Testing (CPT) goes beyond traditional pen testing by using continuous monitoring, vulnerability identification, and validation to strengthen an organization’s defenses. It is used to provide 100% asset discovery, real-time vulnerability detection, remediation guidance, cost and time-saving, reduced risk window, and compliance support to organizations. Here are the business drivers & impact on a CISO:

1. Frequent & Consistent Testing:

Frequent and consistent testing helps uncover and fix weaknesses and operational problems that traditional security tools might miss . This not only reduces downtime but also prevents revenue loss.

2. Automated Pen Testing:

Automated pen testing can quickly identify easy-to-spot issues, it helps catch the obvious problems without needing expensive services.

3. Continuous Breach Validation:

Continuous validation of threat detection and detection tools and response mechanism maximizes breach readiness.

4. Forward Thinking Organizations:

Forward-thinking organizations aim to go beyond the basic compliance requirements and
continuously validate their security posture.

>> To Learn More About Our Continuous Automated Penetration Testing Platform Click here

3 Types of Penetration Testing

1. Black Box Testing

In black box testing, the tester has little to no prior knowledge of the target system. This approach simulates an external cyber-attack where the tester has to gather information about the target, identify vulnerabilities, and attempt to exploit them. It reflects a real-world scenario where an external attacker has limited information about the target system. However, it may take more time to discover vulnerabilities than other testing types.

2. White Box Testing

In white box testing, also known as clear box or glass box testing, the tester has complete knowledge of the target system, including source code, architecture, and infrastructure. This approach simulates an insider threat or an attacker with a detailed understanding of the target. It allows for a comprehensive assessment of the system, including potential vulnerabilities at the code level. However, it assumes a level of internal knowledge that an external attacker might not possess.

3. Grey Box Testing

Grey box testing is a combination of black box and white box testing. The tester has partial knowledge of the target system, usually more than in black-box testing but less than in white-box testing. This approach aims to strike a balance between realism and the depth of analysis. Simulates scenarios where an attacker may have some insider knowledge without complete access. However, it has limited access and may restrict the tester from discovering specific vulnerabilities that a more informed attacker could exploit.

There can be other ways to classify penetration testing as follows:

External Testing vs. Internal Testing:

  • External Testing

    External Testing focuses on assessing the security of externally facing systems, such as web servers, email servers, and firewalls. It simulates attacks from outside the organization.

  • Internal Testing

    Internal Testing involves testing the security of internal systems, typically from the perspective of an authenticated user. This type of testing assesses the potential risks and vulnerabilities that exist within the internal network.

  • Network Penetartion Testing vs. Application Penetration Testing

    • Network Penetration Testing: Focuses on evaluating the security of network infrastructure, including routers, switches, and servers. It aims to identify vulnerabilities that could be exploited to gain unauthorized access to the network.
    • Application Penetration Testing: Concentrates on assessing the security of software applications, web applications, and APIs. The goal is to identify vulnerabilities in the application code, configuration, and logic that attackers could exploit.
  • Red Team vs. Blue Team Exercises

    • Red Team: Simulates a real-world cyber-attack, with the goal of identifying vulnerabilities and weaknesses in the organization’s defenses. The red team acts as the adversary, attempting to breach security.
    • Blue Team: Represents the organization’s defenders and responds to the simulated attack. Blue team exercises focus on detecting, mitigating, and preventing the simulated threats.

Penetration Testing Methodologies

Penetration testing methodologies provide a standardized compass for navigating the complex terrain of target system security. The MITRE ATT&CK framework and the OWASP Web Security Testing Guide are two such methodologies that offer a structured approach to testing and evaluating an organization’s defenses.

These methodologies assist penetration testers and security teams in improving risk assessment and threat hunting, while ensuring their efforts align with the latest in cyber threat intelligence and vulnerability management.

Here are the top five penetration testing methodologies:

1. Open Web Application Security Project (OWASP) testing Guide:

This methodology is designed by the OWASP Foundation, a nonprofit, community-driven organization. It focuses primarily on web applications and their related technologies.

2. Network Penetration Testing:

This involves testing of the internal network, which may include attempting to bypass firewalls or IDS/IDPs or penetrate routers or internal applications.

3. Web Platform Penetration Testing

This involves testing of websites and cloud-based web applications to look for configuration flaws that might leave your externally-facing assets open to breaches.

4. Wireless Penetration Testing:
This is an important form of testing, as improperly secured wireless networks are a major source of security issues for many companies.

5. Social Engineering Penetration Testing:

Human error accounts for a significant number of security breaches, with employees and other users often being susceptible to sharing sensitive information or passwords with stealthy hackers.

What Are The 4 Phases Of Penetration Testing?

The pen testing process progresses through four distinct phases, each vital for comprehensively examining an organization’s security posture. This journey uncovers vulnerabilities and also assesses the organization’s response capabilities, reflecting the stages an actual attacker might undertake.

1. Planning and Reconnaissance

The planning and reconnaissance phase marks the beginning of the pen testing expedition, establishing boundaries and objectives for the security assessment. It’s a phase of gathering intelligence, where information about network topologies, systems, and user accounts is collected, laying the groundwork for a successful penetration test.

2. Vulnerability Identification and Exploitation

Once the groundwork is laid, the subsequent phase involves probing for weaknesses and attempting to exploit them, similar to a predator testing the defenses of its prey. This phase is where the pen testers’ expertise is required, as they utilize both automated tools and their ingenuity to uncover and exploit vulnerabilities that could be leveraged by actual attackers.

3. Access Maintenance and Escalation

The Access Maintenance and Escalation phase includes the following tasks:

  • Maintaining access to the system
  • Escalating privileges without triggering alarms
  • Being stealthy and thorough
  • Ensuring that the discovered vulnerability provides a persistent foothold within the system

This phase truly tests the pen testers’ skills as they strive to gain access, maintain it, and escalate their privileges.

4. Cleanup, Reporting, and Remediation

The concluding phase encompasses cleaning up the post-test, recording all findings, and recommending remediation strategies. It’s a critical step where the lessons learned are translated into actionable improvements, ensuring that the organization can bolster its defenses based on the insights gleaned from the penetration test.

Penetration Testing Tools

>>Top 10 Reconnaissance tools: Download Now

Penetration testing, also known as pen testing, is a crucial aspect of ensuring the security of a network or application. Pen testing tools are an extension of the testers’ hands, each one specialized for a particular aspect of the security assessment. Some common penetration testing tools include:

1. Port Scanning Tools

Tools like Nmap are the eyes of the operation, scanning for open and closed ports that could serve as gateways for unauthorized access. These tools are vital for detecting network vulnerabilities and confirming that all digital doors are adequately secured against potential intruders.

2.Application Scanning Tools

Application scanning tools like ZAP and BURP Suite delve deeper, examining web applications and APIs for security flaws. Operating in real-time, these tools probe for weaknesses while the application functions, assuring early detection and resolution of vulnerabilities.

3. Wireless Network Testing Tools

Wireless networks also undergo scrutiny, with tools such as Wireshark and NetStumbler examining the airwaves for indications of security vulnerabilities. These tools help secure the invisible pathways through which data travels, ensuring that wireless communications remain confidential and protected.

How Frequently Should We Conduct Penetration Testing to Ensure Security?

Integrating a Continuous Penetration Testing tool is advisable, even if point-in-time pen tests or quarterly pen tests are already part of your cybersecurity strategy. Given the dynamic nature of the digital environment, relying on a point-in-time penetration test is insufficient. Conventional penetration testing typically evaluates only a fraction—around 20%—of an organization’s assets during each cycle. Additionally, these tests are typically conducted in isolation, with predefined scopes and timeframes that may not encompass new assets or emerging critical vulnerabilities, potentially leaving security gaps. Attackers exploit brief periods of vulnerability, emphasizing the necessity for ongoing security validation that only continuous penetration testing can provide.

Limitations of Traditional Pen Testing: Why is Traditional Pen Testing Not Good Enough to Prevent Today’s Attacks?

Traditional pen testing, while valuable, comes with limitations such as the time-intensive nature of manual processes and the potential for human error. Traditional Pen Testing is not good enough to prevent breaches for the following key reasons:

1. Outdated or Incomplete CMDB

Organizations either manually update their CMDBs or sporadically use automated tools for comprehensive asset discovery. This approach falls short when considering the dynamic nature of the attack surface and the presence of Shadow IT. These factors often lead to assets being overlooked in vulnerability scans, resulting in CMDBs that are either outdated or incomplete. This oversight increases the risk exposure period to potential attackers.

2.Alert Fatigue

Current vulnerability scanning tools tend to produce a high volume of noise, overwhelming teams with numerous reported vulnerabilities. As indicated by the Common Vulnerability Scoring System (CVSS), the sheer quantity of critical or high-severity vulnerabilities is too vast for timely resolution and remediation. This alert fatigue extends the risk exposure period for critical vulnerabilities to weeks or even months. Techniques such as attack-based vulnerability validation can help reduce noise, but existing scanners do not use them.

3.Manual Pen Testing is Non-Scalable and works in a Silo

Traditional penetration testing methods can typically assess only about 20% of an organization’s assets in a single cycle. Most organizations conduct these tests annually or semi-annually. Furthermore, penetration testing is often conducted in isolation, with a fixed scope and timeframe. For instance, if new assets are added to the Asset Management Solution or critical vulnerabilities are identified, they may have to wait until the next scheduled test for validation.

A company that performs pen tests can bridge this gap by integrating continuous automated pen testing tools.

How is Manual Pen Testing Different From Continuous Pen Testing?

Continuous automated pen testing stands apart from manual pen testing by offering real-time vulnerability detection and remediation. While manual testing is point-in-time, automated testing ensures continuous monitoring and testing, complementing manual methods for a more comprehensive security assessment.


What is the Difference Between Internal and External Penetration Testing?

The difference between internal and external penetration testing lies in their focus and target areas. Internal testing evaluates internal IT infrastructure, while external testing targets external-facing assets or your peripheral assets. An external pen test shows how effective the perimeter security controls are and if they can prevent and detect attacks on internet-facing assets such as cloud buckets, FTP servers, etc. An internal network pen test is performed to understand what an attacker could achieve if they got initial access to a network.


Do I Need a Continuous Pen Testing Solution if I Already Do a Yearly Pen Test?

Yes, you need a Continuous Pen Test tool even if you are doing point-in-time pen tests. In today’s rapidly evolving digital landscape, an annual or a point-in-time pen test would fall short. Firstly, traditional penetration testing methods can typically assess only about 20% of an organization’s assets in a single cycle. Secondly, penetration testing is often conducted in isolation, with a fixed or incomplete scope and a fixed timeframe. For instance, if new assets are added to the Asset Management Solution or critical vulnerabilities are identified, they may have to wait until the next scheduled test for validation. However, attackers are looking for a small window of opportunity and that’s where continuous security validation comes in.


>>Hackers won’t Wait For Your Quarterly Pen Test: Learn More


Are There any Legal Considerations we Should be Aware of Before Conducting Penetration Testing or Continuous Pen Testing?

Before conducting a penetration test, it’s crucial to obtain written consent and define the scope of the test to avoid legal complications. To avoid huge penalties, organizations can employ continuous penetration testing to ensure adherence to regulatory standards like the Payment Card Industry Data Security Standard (PCI DSS) and the Health Insurance Portability and Accountability Act (HIPAA). Continuous Penetration Testing marks a paradigm shift in cybersecurity by embracing a proactive, cyclical approach to security evaluations. By integrating continuous pen testing into their security protocols, organizations can strengthen their defenses in the face of evolving cyber threats while remaining compliant with relevant regulations.


A proactive, continuous approach for penetration testing is essential for safeguarding the constantly changing external attack surface and digital assets. The FireCompass platform performs continuous recon to discover 100% of the Attack Surface and detects delta changes in your attack surface to perform continuous risk hunting. The platform then identifies critical risks within 24 hours through multi-stage attacks using risk-hunting playbooks, mimicking recent threat actors. Some of the playbooks include ransomware, LOG4J, CISA Alerts, critical infrastructure, web applications, stolen credentials, and social engineering. The platform further exploits CVEs to validate risks, and credential attacks to identify credential exposure, and gains an initial access point to validate security controls.