Understanding Penetration Testing: Key to Robust

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What is Penetration Testing?

Penetration testing, also known as a pentest or ethical hacking, is an authorized simulated cyberattack on a computer system, performed to evaluate the security of the system. The goal is to identify both weaknesses (also referred to as vulnerabilities), including the potential for unauthorized parties to gain access to the system’s features and data, as well as strengths, enabling a full risk assessment.

Pentests attempt to simulate the actions of a real attacker to identify methods a malicious hacker could use to exploit the system. However, pentesting is conducted in a controlled manner with prior permission from system owners. Ethical hackers performing pentests use the same methods and tools as criminal hackers, but focus strictly on evaluating the security posture of a target system.

The key characteristics that define penetration testing include:

  • Authorized – Pentests are performed with permission from system owners to avoid violating laws or unnecessary damage.
  • Simulated Attack – The pentest attempts to mimic the techniques of real attackers to identify authentic vulnerabilities.
  • Evaluative – The goal is to assess and report on the security of the target system.
  • Controlled – Pentests are done in a planned, safe, and systematic methodology.

The insights gained from a properly executed penetration test can help organizations understand their true security risks, prioritize remediation efforts, and improve defenses against real-world attacks.

Why Use a Penetration Testing Service?

Organizations should consider using a penetration testing service for several important reasons:

  • Identify Vulnerabilities Proactively: Penetration testing helps uncover weaknesses in systems, applications, networks, and physical security before they are discovered and exploited by hackers. Finding and fixing vulnerabilities proactively is far better than dealing with the aftermath of an attack.
  • Strengthen Defenses: The findings from penetration tests allow organizations to improve their security measures, close loopholes, and block attack vectors. This hardens the organization’s defenses and makes them more resilient to threats.
  • Required for Compliance: Many industry compliance standards and regulations like PCI DSS, HIPAA, FFIEC, etc. require recurring penetration testing. Organizations need to conduct tests regularly to satisfy compliance requirements.
  • Avoid Data Breaches: Penetration testing reduces the risk of cyber attacks that can lead to data breaches, theft of sensitive information, outages, and monetary losses. Identifying and closing security gaps is one of the best ways to prevent breaches.

In summary, penetration testing services provide immense value for organizations by allowing them to find and remediate security issues before hackers do. They strengthen defenses, satisfy compliance needs, and help avoid disastrous data breaches.

Types of Penetration Tests

Penetration testing services offer various types of assessments tailored to an organization’s specific security needs and goals. Some common types of pen tests include:

Network Penetration Testing

Tests internal networks to find vulnerabilities that could allow unauthorized access. This simulates an attack from inside the network perimeter and assesses risks to servers, computers, routers, firewalls, switches and other infrastructure.

Web Application Penetration Testing

Analyzes web apps and APIs to uncover flaws like SQL injection, cross-site scripting (XSS), broken authentication, and improper access control. Tests customer-facing apps as well as internal tools.

Mobile Application Penetration Testing

Assesses mobile apps for issues like insecure data storage, lack of binary protection, and weak session management. Tests apps on iOS, Android, Windows Mobile and other mobile platforms.

Social Engineering Testing

Targets employees to evaluate human weaknesses that could be exploited, like phishing emails and fraudulent phone calls asking for sensitive data. Helps strengthen security awareness.

Wireless Penetration Testing

Identifies vulnerabilities in Wi-Fi, Bluetooth, NFC and other wireless systems, including weak encryption, default passwords, and improper access control.

Physical Penetration Testing

Attempts unauthorized physical access to facilities to bypass physical security controls. Tests doors, windows, fences and other entry points. Identifies risks and improvements.

Penetration Testing Methodology

A penetration test typically involves the following phases:

Information Gathering

This involves gathering publicly available information about the target organization from sources like social media, job postings, website subdomains, and open databases. The goal is to discover information that can aid in the penetration test like network architecture, IP addresses, technologies used, and even usernames.


In this phase, the penetration tester scans the organization’s systems and infrastructure to discover vulnerabilities. This may involve port scanning, banner grabbing, service enumeration, and operating system fingerprinting. The tester is looking for misconfigurations, unpatched systems, and exploitable services.


The penetration tester now attempts to exploit any vulnerabilities discovered in the previous phases to gain access to systems and data. This may involve exploiting unpatched software vulnerabilities, weak credentials, default accounts, and misconfigurations. The goal is to obtain unauthorized access and elevate privileges.


After gaining access, the tester pivots throughout the network, escalates privileges, and exfiltrates data to determine the full impact an attacker could have. The tester may implant backdoors, capture screenshots, enumerate software/patches, and more.


The final phase involves documenting all findings and creating a report for the client. This details the vulnerabilities discovered, the access/data obtained, remediation recommendations, and an executive summary. Reports aim to help organizations improve their security posture.

Penetration Testing Tools

Penetration testers rely on various tools and software to identify vulnerabilities and security issues in systems and applications. Some of the most common and powerful penetration testing tools include:

Kali Linux

Kali Linux is a Debian-based Linux distribution designed specifically for penetration testing and security auditing. It comes preinstalled with hundreds of tools for information gathering, vulnerability assessment, exploitation, password cracking, web app analysis, and more. Kali Linux is a go-to platform for many penetration testers.


Metasploit is an open source penetration testing framework that contains thousands of known exploits and payloads. It can be used to automate the exploitation of known vulnerabilities and security misconfigurations. Metasploit also contains useful tools for reconnaissance and evasion.


Nmap is a network scanner used to discover hosts, services, OS versions, and vulnerabilities on a network. Nmap can reveal the open ports and services running on target systems through port scanning. It’s an essential tool for network mapping and service discovery during a penetration test.

Burp Suite

Burp Suite is an integrated platform for web application security testing. Its tools work together to support the entire testing process, including advanced manual inspection of web requests/responses, vulnerability scanning, and automation. Burp is often used for in-depth testing of web apps and APIs.


The OWASP Zed Attack Proxy (ZAP) is a free and open source web app scanner. It can automatically find vulnerabilities like XSS, broken authentication, and code injection in web applications. ZAP offers automated and manual attack modes, proxy functionality, useful reporting, and more.

John the Ripper

John the Ripper is a fast password cracker used to test password strength and authentication mechanisms. By cracking hashed passwords, it can highlight weak credentials and insecure password policies. John the Ripper can integrate with other tools to use extracted password hashes.

These and many other tools are leveraged during penetration tests to identify security issues before hackers do. Skilled penetration testers can use these tools effectively to provide an accurate picture of risk and prioritized vulnerabilities.

How to Choose a Penetration Testing Company

When selecting a penetration testing service, it’s important to vet potential providers thoroughly. Here are some key factors to consider:

Industry Experience

Look for companies with at least 5 years of experience performing penetration tests. They should have a proven track record with a variety of clients across multiple industries. More experience means they will be familiar with different environments and better able to identify vulnerabilities.


Choose a company whose testers hold industry certifications like CEH, OSCP, GPEN, GWAPT. This validates their skills and methodology. Requiring certifications also indicates they invest in ongoing tester training.


Ask about their methodology and ensure it aligns with standards like NIST 800-115. Look for a systematic approach that includes planning, discovery, attack, reporting, and retesting phases. Their methodology should be repeatable and customized to your environment.


The penetration test report is one of the most important deliverables. It should provide technical details of vulnerabilities found along with remediation guidance, proof-of-concept examples, and risk ratings. Reports should be well-organized and presented with an executive summary.

Customer Service

Work with a provider who values customer service. Look for quick response times and dedicated points of contact. They should listen to your requirements and keep you updated throughout the process. Strong communication means a more effective test and actionable results.

Choosing the right penetration testing company takes research. Prioritize industry experience, certifications, methodology, reporting, and customer service when evaluating providers. This helps ensure an effective test that delivers maximum value.

Penetration Testing Standards

Penetration testing services adhere to industry standards and best practices to ensure high quality, thorough security assessments. Some key standards include:

  • OWASP Testing Guide – The Open Web Application Security Project (OWASP) provides a comprehensive testing guide outlining techniques for evaluating vulnerabilities in web apps and APIs. It covers testing methods for injection, authentication, access control, and more.
  • PCI DSS – The Payment Card Industry Data Security Standard (PCI DSS) is a set of security requirements for businesses that handle credit cards. It mandates external penetration testing for Level 1 merchants annually and after significant infrastructure changes.
  • NIST – The National Institute of Standards and Technology (NIST) publishes a risk assessment framework, Special Publication 800-115, outlining technical security testing methodology for federal information systems.
  • OSSTMM – The Open Source Security Testing Methodology Manual (OSSTMM) developed by the Institute for Security and Open Methodologies (ISECOM) provides best practices for thorough security testing and risk analysis.

Reputable penetration testing companies will follow approaches aligned with these methodologies and standards. Adhering to industry norms ensures penetration testing adequately evaluates vulnerabilities, providing clients an accurate view of security risks and actionable remediation guidance.

Penetration Testing Limitations

While penetration testing is an invaluable security practice, it does have some inherent limitations to be aware of:

  • Point-in-time assessment: Penetration tests provide a snapshot of an application or system’s security posture at a specific point in time. Threats and vulnerabilities are continuously evolving, so the results may not fully reflect the current security state. Regular testing is recommended to get a more complete picture.
  • Dependent on tester skills: The success of a penetration test relies heavily on the skills and experience of the security tester. An inexperienced tester may miss vulnerabilities that a more seasoned professional would detect. Organizations should thoroughly vet the capabilities of third-party testing firms.
  • Bypass advanced defenses: Sophisticated attackers may have tools and techniques that allow them to bypass certain defensive controls and protections. A standard penetration test may not be able to replicate these methods. Organizations should consider more advanced red team exercises as well.

While these limitations exist, penetration testing remains an invaluable practice. Organizations can maximize effectiveness by conducting frequent, comprehensive tests using skilled testers, and combining penetration testing with other assessments and security measures. But it’s important to understand that a penetration test is not a silver bullet. A strong cybersecurity strategy requires continuous monitoring, defense-in-depth protections, and security awareness across the organization.

Improving Penetration Testing Effectiveness

Penetration testing can provide immense value for securing infrastructure and applications, but to maximize effectiveness, certain best practices should be followed:

Realistic Scope

Define a realistic scope and set of objectives for testing based on business risks, major vulnerabilities, and critical assets. Attempting to test everything superficially dilutes the penetration test’s thoroughness. Prioritize testing what matters most.

Continuous Testing

Conduct testing regularly, not just once. Systems and environments constantly change and new threats emerge. Frequent penetration testing catches issues before they’re exploited. Integrate testing into development pipelines and operations.

Integrate Findings

Don’t silo penetration test reports. Integrate findings into vulnerability management programs. Track issues over time, measure improvements, and feed results into development, ops, and security operations.

Purple Teaming

Perform purple team exercises by having penetration testers attack live while defenders detect and respond. This aligns technical, process, and communication workflows for real incident response capabilities.

By focusing testing on prioritized assets, repeating it continuously, integrating findings across tools and teams, and sharpening live response, organizations can maximize the value gained from investment in penetration testing services. Testing informs actionable improvements to strengthen security posture over time.

Penetration Testing Costs

Penetration testing can vary greatly in cost depending on several factors:

  • Size of the organization – Pen testing a large enterprise with thousands of employees, multiple offices, and a global footprint will cost more than a small business with just a single office. More users, devices, networks, and systems to test means higher costs.
  • Scope of the test – The breadth and depth of what’s included in the pen test impacts costs. Testing everything from external networks, web apps, mobile apps, wireless networks, social engineering, physical access, etc. is more expensive than just focusing on one area like external infrastructure.
  • Location – Testing systems and offices in multiple geographic regions can increase travel costs for on-site testing. Companies with a global presence may need to budget more compared to a single location.
  • Complexity – Highly complex environments with many interdependencies, custom apps, legacy systems, and specialized technologies can increase the expertise required and make testing more effort intensive. More complex, means higher cost.
  • Managed services vs project-based – Ongoing managed pen testing services that include recurring tests on a monthly/quarterly basis tend to cost less per test than one-off project-based engagements. The fixed fee for managed services spreads out costs over time.
  • Company size and reputation – Large, well-known cybersecurity firms often charge more for their services than independent consultants or newer companies. The brand name and reputation adds cost.

While each pen test is different, most fall in the range of $5,000-$50,000+ depending on the above factors. The more in-depth the test, and the larger the company, the more it will cost. Companies should balance cost against potential risk when budgeting for cybersecurity.