The Difference Between a Good and Bad Pentest

Pen testing is very important to a company’s security as it identifies vulnerabilities before attackers can exploit them. It also reduces potential financial and reputational damages from breaches and meets regulatory requirements like GDPR, HIPAA, and PCI DSS. Good pen testing is crucial to enhance organizational security and reduce overall risk of cyber attacks as they are quite frequent in today’s digital age. Completing pen testing regularly makes it easier to handle evolving cyber threats and helps organizations find problems before attackers can take advantage of them.

Penetration testing is a critical component of modern cybersecurity strategies to identify and address vulnerabilities in an organization’s systems. However, not all penetration tests are created equal. The distinction between good and bad penetration testing is in the approach, and the execution. It is vital to understand these differences to ensure that your organization receives maximum security.

Good Penetration Testing

Good penetration testing is comprehensive and follows an organization’s specific security needs. It follows established frameworks such as the Open Web Application Security Project (OWASP) or the Penetration Testing Execution Standard (PTES) for a structured approach. A good pen test is executed by certified professionals with extensive knowledge of cybersecurity practices and attack methods. These professionals simulate real-world attacks and examine systems for vulnerabilities like misconfigurations, weak passwords, unpatched software, and insecure network protocols.

Good penetration testing is about identifying vulnerabilities and providing detailed and actionable reporting at the conclusion of the test. Effective reports include the following components:

• A clear explanation of identified vulnerabilities: Each vulnerability is described in detail, explaining what it is, how it works, and why it poses a risk to the organization’s systems. This makes sure that stakeholders understand the nature of the threat.

• Risk ratings to prioritize remediation efforts: Each vulnerability is assigned a risk rating (low, medium, high, or critical) to help the organization prioritize remediation based on the severity of the potential impact.

• Specific recommendations for mitigating risks: The report provides clear, actionable steps to resolve each identified issue. This may include patch updates, configuration changes, or advice on secure coding practices.

• Supporting evidence to validate findings: The findings are backed by evidence, such as screenshots, logs, or proof-of-concept exploits. This demonstrates how the vulnerability was discovered and why it is legitimate.

Good penetration testing identifies weaknesses, but most importantly, it provides a roadmap for strengthening an organization’s cybersecurity posture. This ensures that identified issues can be resolved efficiently and effectively.

Good Penetration Testing as a Detective Investigation

Think of a good penetration test as a police investigation conducted by expert detectives. We aim to uncover weaknesses in an organization's defenses before a criminal (cyber attacker) strikes. Similar to a thorough investigation, a pen test follows a methodical process:

1. Reconnaissance: The Detective’s Background Check

This is where the "detectives" (penetration testers) gather intelligence about the "suspect" (the target system or network). They dig into the system's data structure, identify the technologies used, and uncover any potential vulnerabilities. Similar to how detectives collect witness statements, public records, and patterns of criminal behavior, testers map out the system’s landscape to find areas worth investigating.

2. Scanning: Dusting for Fingerprints

With the intel collected, the testers begin scanning the system, much like detectives use tools to search for clues. They examine the system for open ports, active services, and weak points in the infrastructure like dusting for fingerprints or using high-tech devices to detect hidden evidence. These scans highlight areas where an attacker might slip through the cracks.

3. Exploitation: Simulating the Crime Scene

Once the vulnerabilities are identified, the testers move to exploitation, where they simulate real-world attacks. This is like how detectives might stage a reenactment of a crime. They attempt to exploit the weaknesses they found, imitating the steps an actual attacker would take to breach the system. This step uncovers critical flaws, showing how much damage an attacker could do if left unchecked.

4. Post-Exploitation: Understanding the Crime’s Impact

After "committing the crime," the detectives analyze the aftermath. Testers assess the impact of their exploitation—what data they could access, how far they could go, and how the weaknesses could jeopardize the organization. This is akin to detectives piecing together the motive and plan of action of a criminal to understand the full scope of the danger.

5. Reporting: The Case File

Finally, the detectives compile a comprehensive case file, just like pen testers create a detailed report. This report includes:

• A clear explanation of the findings: What "crimes" (vulnerabilities) were discovered and how they could harm the organization.

• Risk ratings: Prioritizing the issues based on their severity.

• Recommendations: Specific steps to "close the case" by fixing the vulnerabilities.

• Evidence: Logs, screenshots, and proof-of-concept exploits to back up their findings.

Just as a good detective uncovers the truth and prevents future crimes, a good pen test ensures that an organization's systems are secured, helping to prevent potential cyber breaches. Both rely on meticulous processes, sharp instincts, and actionable insights to deliver the best outcomes.

Good penetration testing has great communication and collaboration throughout the process. Testers work closely with the organization’s IT and security teams to have transparency with their objectives. A good pen test is ethical and follows pre-defined scopes, so testing activities do not disrupt normal business operations.

Bad Penetration Testing as a Failed Investigation

Bad penetration testing is like a sloppy investigation where the "detectives" (testers) lack thoroughness, expertise, and professionalism. Instead of uncovering the truth, it leaves organizations with incomplete results and misguided confidence in their security. Here are the key issues with bad penetration testing:

1. Overreliance on Automated Tools

Bad pen tests often depend heavily on automated scanning tools without any manual verification. While automated tools can identify basic vulnerabilities, they fail to uncover complex issues that require critical thinking and in-depth analysis. This results in incomplete or inaccurate findings that leave significant security gaps undetected.

2. Poor Communication and Lack of Stakeholder Alignment

A hallmark of bad penetration testing is the lack of clear communication between the testers and the organization. Without stakeholder alignment, testers operate in isolation, failing to account for the organization's specific needs and risk priorities. They do not set a clear time frame for testing or notify the client about critical phases of the process. This lack of transparency leaves clients uninformed about what is happening, when it is happening, or why certain tests are being performed.

3. Disorganization and Vague Methodology

Bad pen tests are often disorganized, lacking a structured approach or adherence to established frameworks like OWASP or PTES. The absence of a clear methodology leads to incomplete testing, missed vulnerabilities, and a chaotic process that causes confusion for all parties involved. Even worse, disorganized testing can lead to unintentional disruptions, such as taking down a server, corrupting data, or impacting business operations.

4. Unqualified Testers and Ineffective Simulations

Unqualified testers (those without proper certifications or experience) struggle to simulate real-world attacks effectively. Their lack of expertise can lead to false positives (identifying issues that don’t exist) or false negatives (missing critical vulnerabilities altogether). This gives organizations a false sense of security, believing they are protected when they are not.

5. Generic and Unclear Reporting

Bad penetration tests produce generic reports that prioritize style over substance. These reports often:

• Lack actionable insights, making it difficult for organizations to address issues.

• Provide unclear findings that leave clients confused about what vulnerabilities were identified and why they matter.

• Fail to include risk ratings or prioritization, leaving organizations unsure of what to fix first.

6. Potential for Damage

Inadequate testing processes can lead to unintended consequences. For example, poorly executed tests might cause servers to crash, corrupt sensitive data, or disrupt critical business functions. Instead of improving security, bad pen tests might inadvertently introduce new risks or damage an organization's operations and reputation.

Without actionable insights, clear communication, and a structured methodology, these tests fail to address the core security needs of the organization. Worse, they can cause operational disruptions, leaving businesses in a weaker position than before the test began. A good pen test, by contrast, prioritizes transparency, expertise, and professionalism, ensuring that vulnerabilities are identified and addressed in a way that strengthens the organization's overall cybersecurity posture.

By selecting qualified professionals at Last Tower Solutions, we adhere to established methodologies and emphasize clear communication with our clients. Organizations can ensure that our penetration testing follows best practices to assist you in securing your company.