Penetration Testing in Your Organization: Complete 2025 Guide

Why Companies Perform Pen Tests

Companies perform penetration tests to strengthen their defenses against cyber threats, ensuring that any existing vulnerabilities are identified and mitigated before cybercriminals can exploit them. A thorough pen test exposes weaknesses within IT infrastructure, applications, or networks, allowing for timely corrections to prevent data breaches and financial losses.

Regular penetration testing helps organizations comply with industry standards and regulatory requirements, which often mandate such assessments to protect sensitive data. By engaging in pen testing, companies defend their assets and build trust with clients and stakeholders. Pen tests serve as a tool in risk management by preemptively addressing threats.

Types of Penetration Testing 

External Testing

External testing, also known as external network penetration testing, assesses the security of publicly visible points on an organization’s external infrastructure, such as websites, emails, and networks. The goal is to identify vulnerabilities that could be exploited by attackers from outside the organization.

During external testing, testers prioritize attack vectors accessible from the Internet, with particular focus on applications and servers that handle critical business operations. Such tests highlight weaknesses in a company’s firewall, DNS, and web hosting services.

Internal Testing

Internal testing assesses security from within the organization, simulating an attack scenario where the perpetrator has inside access, potentially as a disgruntled employee or a simulated user. It reveals how much damage an attacker could inflict with internal system access.

This type of testing evaluates security protocols in place to prevent or mitigate insider threats, examining network segmentation, internal controls, and sensitive data access. The results of internal testing provide insights on potential abuse of access rights, misuse of permissions, and other internal threats. 

Blind Testing

Blind testing, or black-box testing, is a method where the penetration tester has very limited knowledge of the target system or network. This simulates the techniques a real-world attacker would use when approaching a network they're unfamiliar with. Testers rely on reconnaissance, using publicly available information to identify possible vulnerabilities without insider information.

This type of testing highlights how effectively an organization can detect and respond to unexpected attack attempts. It provides insights into real-time detection capabilities and response protocols. 

Double-Blind Testing

Double-blind testing, also known as no prior knowledge testing, takes blind testing a step further by keeping not only the testers but also the internal security team in the dark about the test’s details. This setup creates a true-to-life scenario where security personnel must identify, defend against, and counteract the simulated attack without forewarning. 

This method evaluates the organization's real-time response and detection capabilities. It tests the readiness of security teams under untested scenarios, ensuring they can manage unexpected breaches. 

Targeted Testing

Targeted testing, often called collaborative pen testing or white-box testing, involves a cooperative approach where both the tester and the internal IT team know the test's objectives. The method involves clearly defined goals, such as testing the strength of specific applications or network segments. 

Targeted testing is beneficial for assessing scenarios where the organization needs to verify security measures or harden certain parts of their infrastructure. Organizations often use targeted testing to test new systems or updates before wide-scale deployment.

Network Penetration Testing

Network penetration testing involves evaluating an organization's network infrastructure to identify security gaps that could be exploited for unauthorized access. This testing assesses devices including routers, switches, and firewalls, checking for configuration weaknesses and outdated software. 

Pen testers use various techniques to expose security weaknesses, such as packet sniffing, scanning, and vulnerability exploitation. The process generates a report detailing identified vulnerabilities and actionable insights to enhance security. 

Web Application Penetration Testing

Web application penetration testing focuses on assessing web apps for vulnerabilities such as SQL injection, cross-site scripting, and insecure configurations. Applications often house sensitive data, requiring thorough testing to identify and mitigate risks that could lead to data breaches and unauthorized access. 

Web app tests help ensure secure interactions between the application and its users. Testers simulate real-world attack scenarios, evaluating application security from both authenticated and unauthenticated perspectives. 

Social Engineering Penetration Testing

Social engineering penetration testing attempts to exploit human factors rather than technical vulnerabilities. It simulates techniques attackers use to trick employees into disclosing sensitive information or committing unauthorized actions. 

Common approaches include phishing, baiting, and impersonation. These tests assess how susceptible organizational personnel are to social manipulation. The insights from social engineering tests help organizations adjust their security culture, training employees to recognize and resist manipulation attempts. 

Physical Penetration Testing

Physical penetration testing evaluates an organization’s physical security controls, determining how effectively they prevent unauthorized access. Testers attempt to infiltrate buildings, restricted areas, and sensitive areas, using stealth methods akin to those employed by real-world intruders. 

This testing examines access controls, surveillance, alarms, and physical barriers. The test results identify physical security vulnerabilities that could lead to unauthorized data access or asset theft. Organizations benefit by reinforcing security policies, enhancing physical deterrents, and training personnel in security practices. 

Related content: Read our guide to API attacks

Tzvika Shneider

CEO, Pynt

Tzvika Shneider is a 20-year software Security industry leader with a robust background in product and software management.

Tips from the expert

• Use threat intelligence to prioritize testing targets: Incorporate real-world threat intelligence to focus tests on the most likely attack paths or exploit scenarios relevant to the industry. This approach can improve test relevance and help simulate realistic attack methods attackers might employ.
• Test against privilege escalation pathways: Many breaches result from attackers moving from low-privilege to high-privilege accounts. Beyond perimeter and external defenses, test user role configurations and privilege escalation possibilities to identify risks that might otherwise go unnoticed.
• Establish a ‘red team’ feedback loop with incident response: To maximize insight, coordinate penetration tests (especially double-blind tests) with the incident response team, treating them as a red team. This collaboration strengthens detection and reaction capabilities by revealing response gaps and informing playbook enhancements.
• Prioritize testing of third-party integrations and APIs: APIs and third-party services are frequent attack vectors but are often missed in standard pen testing. Expand testing to include API endpoints, third-party application connections, and service configurations, as these can introduce unexpected vulnerabilities.
• Simulate DDoS attacks on critical applications: Many penetration tests overlook Distributed Denial of Service (DDoS) scenarios that can cripple applications or networks. Include simulated DDoS attempts to assess resilience and response plans under high-traffic conditions.

Penetration Testing Methodologies 

Planning and Reconnaissance

During this phase, testers gather intelligence on the target system to identify potential entry points and vulnerabilities. This involves collecting information about the organization's network architecture, domain details, IP addresses, and operating systems, often through publicly accessible sources and tools like whois, DNS, and social media.

Meticulous planning and data collection enable testers to design targeted attack strategies, maximizing the effectiveness of subsequent penetration attempts. Organizations gain insights into what potential attackers may already know about their systems. 

Scanning and Enumeration

Scanning and enumeration follow the initial reconnaissance phase, focusing on probing the target system for open ports, services, and potential vulnerabilities. During this phase, testers use tools like network scanners, vulnerability scanners, and port scanners to map out the network's topology and identify exploitable entry points. 

Enumeration goes a step further by identifying user accounts, machine names, and other network directories to understand the network better. By probing deeper into the network layer, testers detail the attack surfaces available for exploitation. 

Exploitation

Exploitation is the phase where testers actively attempt to leverage detected vulnerabilities to gain unauthorized access or extract information. This step is crucial for demonstrating the potential real-world impact of security flaws. Testers employ various methods to exploit weaknesses, simulating potential steps an actual attacker might take to achieve their objectives.

This hands-on testing reveals the extent to which vulnerabilities can be abused, guiding IT teams in prioritizing remediation efforts. It reveals the severity of each weakness by demonstrating potential data breaches or the compromise of critical systems. 

Post-Exploitation

The post-exploitation phase involves analyzing and documenting the activities that can be conducted after gaining access to a compromised system. Testers assess the range of actions possible, such as maintaining access, escalating privileges, and moving laterally within the network. 

The insights from post-exploitation highlight the potential impact of cyber intrusions and inform the development of incident response protocols. Organizations can identify gaps in detection and containment strategies, helping improve long-term resilience against advanced persistent threats. 

Reporting and Remediation

Reporting and remediation are the final steps in penetration testing, where findings are documented and mitigation strategies are proposed. Detailed reports outline every identified vulnerability, potential impact, and recommended fixes. These reports offer a clear picture of the organization's security posture and necessary remediation actions.

Remediation involves addressing the identified vulnerabilities, either by applying security patches, reconfiguring systems, or enhancing security controls. Testers collaborate with security teams to ensure that vulnerabilities are effectively mitigated. 

Types of Penetration Testing Tools 

Manual Penetration Testing Tools

Manual penetration testing tools enable testers to conduct customized, hands-on assessments that reveal vulnerabilities often overlooked by automated systems. These tools give testers the flexibility to perform in-depth analyses of targeted areas, applying techniques and human intuition to uncover subtle security gaps. 

Testers can manually explore applications, networks, and configurations, simulating real-world attack scenarios in a controlled, adaptive manner. This approach is especially valuable in complex or high-stakes environments where granular control is necessary to identify risks that automated scans may miss. 

Automated Penetration Testing Tools

Automated penetration testing tools help organizations scale their security assessments by conducting large-scale vulnerability scans and analyses quickly and systematically. These tools leverage scripts, algorithms, and predefined checks to cover extensive systems and networks in a fraction of the time required for manual testing. 

By identifying common vulnerabilities such as weak configurations, outdated software, and unpatched systems, automated tools enable fast baseline security assessments. However, automated tools primarily focus on known vulnerabilities and standardized checks, making them suitable for regular, compliance-focused testing. 

Penetration Testing as a Service (PTaaS)

Penetration testing as a service (PTaaS) is a flexible, cloud-based solution that offers on-demand access to automated and manual pen testing capabilities without dedicated in-house infrastructure or specialized technical staff. PTaaS platforms provide organizations with tools, resources, and access to skilled testers, making it easier to manage tests remotely. 

Through PTaaS, users can monitor testing progress, view real-time reporting, and track vulnerabilities across systems, often with integration into broader security management platforms. 

Challenges in Penetration Testing 

Organizations should also be aware of the potential challenges associated with pen testing:

• Legal and ethical considerations: Organizations must ensure that all testing activities are fully authorized, complying with applicable laws and policies. Testers are bound by ethical practices, maintaining the confidentiality and integrity of tested information, alongside not causing any harm intentionally.
• False positives and negatives: False positives occur when a test incorrectly identifies a vulnerability, wasting resources on non-issues. False negatives are more dangerous, omitting real vulnerabilities that remain unaddressed. Both scenarios can hinder an accurate understanding of the organization's security posture.
• Resource constraints: Effective penetration testing demands skilled personnel, time, and financial investment. Organizations often struggle to allocate sufficient resources, impacting the depth and frequency of tests. Insufficient resources may lead to incomplete tests, missing critical vulnerabilities, or less effective testing methodologies.

Penetration Testing Best Practices 

Here are some of the ways that organizations can ensure the most effective pen testing strategy.

Define Clear Objectives and Scope

Establishing precise goals helps allocate resources and align testing activities with business needs. Defining the scope prevents unnecessary disruptions or unintentional testing actions, allowing testers to concentrate on the most relevant systems, applications, or networks.

A well-defined scope creates a structured approach, reducing ambiguity for testers and safeguarding critical systems from inadvertent impact during tests. Detailed scope definitions help organizations prioritize areas with significant risk exposure, increasing the efficiency and productivity of the testing process. 

Obtain Proper Authorization

Organizations must secure formal permission from stakeholders or designated authorities before commencing tests. Such approvals define the boundaries of the test, providing legal protection and ensuring compliance with internal policies and relevant laws, avoiding unintended legal consequences.

Authorization establishes trust between testers and the organization, enabling open communication channels and support throughout the process. It also requires clear documentation and agreements specifying the rights and restrictions of the testing parties. 

Use Skilled and Certified Testers

Professionals with recognized certifications like OSCP, CEH, or CISSP have proven expertise, equipped with the necessary skills and knowledge of current threat landscapes. Hiring certified testers enhances the reliability and credibility of testing results, ensuring a comprehensive evaluation.

Experienced testers can perform analysis and uncover more sophisticated vulnerabilities that uncertified personnel may overlook. Certified professionals also adhere to standardized methodologies, contributing to the repeatability and trustworthiness of test outcomes. 

Regularly Update and Repeat Tests

As new threats and vulnerabilities emerge, previously completed penetration tests can quickly become outdated. By scheduling regular assessments, organizations can address new risks and adapt to changes in their IT environments, ensuring continuous protection.

The iterative approach of repeating tests enables organizations to track the efficacy of remediation efforts and verify the persistence of implemented security measures. Regular testing cultivates a proactive security culture, where adjustments to strategies and systems can be made in response to routine operations and emerging cybersecurity challenges.

Integrate Pen Testing with the Security Strategy

Pen tests should align with wider security initiatives to maximize their value. Continuous integration of test results into security programs fosters a culture of security awareness and action, embedding pen testing insights into broader organizational risk reduction plans.

Pen testing integration requires collaboration between security teams, IT departments, and organizational leadership, ensuring findings are acted upon consistently and timely. It encourages the adaptation of security policies and procedures based on real-time data. 

Supporting Penetration Testing with Pynt Automated Security Testing

Pynt complements and enhances traditional penetration testing by providing automated, continuous security testing directly within the development lifecycle. With Pynt, you gain deeper coverage and faster detection of vulnerabilities, reducing reliance on periodic manual testing while ensuring that critical issues are found and addressed promptly.

Our platform delivers contextual, AI-driven insights that highlight genuinely exploitable issues across applications, APIs, and beyond. Pynt covers the OWASP Top-10 for APIs, web applications, and emerging technologies like LLMs, allowing teams to stay ahead of evolving threats. Seamlessly integrating into CI/CD pipelines, Pynt automates vulnerability detection, aligning with DevOps practices for shift-left security.

For more details on how Pynt can elevate your security testing, visit Pynt.io.