What is Penetration Testing and How Does It Work?

A penetration test, also known as a pen test, is an attempt to evaluate the security of an IT infrastructure by exploiting vulnerabilities safely. These flaws can exist in operating systems, services and applications, incorrect configurations, or risky end-user behaviour. Such assessments can also be used to validate the effectiveness of defensive mechanisms and end-user adherence to security policies. Manual or automated technologies are typically used in penetration testing to systematically compromise servers, endpoints, web applications, wireless networks, network devices, mobile devices, and other potential points of exposure. Once vulnerabilities on a specific system have been successfully exploited. Testers may attempt to use the compromised system to launch subsequent exploits at other internal resources. Specifically by attempting to incrementally achieve higher levels of security clearance and deeper access to electronic assets and information via privilege escalation.

Information about any security vulnerabilities exploited successfully through penetration testing is typically aggregated. And presented to IT and network system managers to assist those professionals in reaching strategic conclusions and prioritizing related remediation efforts. The primary goal of penetration testing is to assess the feasibility of system or end-user compromise and to assess the impact such incidents may have on the involved resources or operations.

It might be helpful to think of penetration testing as attempting to break into your house by yourself. Penetration testers, also known as ethical hackers, assess the security of IT infrastructures by attacking, identifying, and exploiting vulnerabilities in a controlled environment. Instead of inspecting the windows and doors, they examine servers, networks, web applications, mobile devices, and other potential entry points for flaws.

How Does a Penetration Test Work?

There is no one comprehensive testing method that everyone uses for penetration testing. Part of this is because cyber threats are constantly evolving, and pen tests must simulate whatever attack methods the organization is likely to encounter.

A penetration test’s “broad strokes” include the following:

1. Assigning a person or group to act as “white hat” hacker(s) to carry out the test on a randomized date and time.
2. Members of the vulnerability management team scan the IP addresses of various assets on the network to identify assets. That use services or operating systems with known vulnerabilities.
3. The penetration testing team carried out a series of simulated attacks on the network using various attack methods. These attacks could target known vulnerabilities discovered during the preliminary scan.
4. As if the attack were real, the organisation is attempting to contain, stop, and investigate it (depending on how the attack is conducted. The cybersecurity team may not know it is a pen test instead of a real attack).

The pen test team must exercise caution when carrying out the test. If the test is performed incorrectly, it may cause actual damage to the target systems. Resulting in network congestion or system crashes for some network assets.

It can also be broken down into different stages:

Reconnaissance and planning

The first stage entails the following:

• Defining the scope and objectives of a test, including the systems to be tested and the testing methods to be used.
• Obtaining intelligence (e.g., network and domain names, mail server) to better understand how a target works and its potential vulnerabilities.

Scanning

The following step is to determine how the target application will react to various intrusion attempts. This is usually done with:

• Static analysis is the process of inspecting an application’s code to estimate how it will behave while running. These tools are capable of scanning the entire code in a single pass.
• Dynamic analysis entails inspecting an application’s code while it is running. This method of scanning is more practical, as it provides a real-time view of an application’s performance.

Getting Access

This stage employs web application attacks such as cross-site scripting, SQL injection, and backdoors to identify vulnerabilities in a target. To understand the damage that these vulnerabilities can cause, testers attempt to exploit them by escalating privileges, stealing data, intercepting traffic, and so on.

Continuing to have access

The goal of this stage is to determine whether the vulnerability can be exploited to maintain a persistent presence in the exploited system long enough for a bad actor to gain in-depth access. The goal is to mimic advanced persistent threats, which can stay in a system for months while stealing an organization’s most sensitive data.

Analysis

The penetration test results are then compiled into a report that includes the following information:

• Specific flaws that were exploited
• Access to sensitive data
• The length of time the pen tester was able to remain undetected in the system.

Security personnel use this data to help configure an enterprise’s WAF settings and other application security solutions to patch vulnerabilities and protect against future attacks.

Methods of penetration testing

• External evaluation
  External penetration tests target a company’s internet-visible assets, such as the web application itself, the company website, and email and domain name servers (DNS). The goal is to obtain and extract valuable data.

• Internal evaluation
  In an internal test, a tester with access to an application behind the company’s firewall simulates a malicious insider attack. This is not always simulating a rogue employee. A common starting point is an employee whose credentials were stolen as a result of a phishing attack.

• Blind evaluation
  A blind test gives a tester only the name of the enterprise being targeted. This provides security personnel with a real-time view of how an actual application attack would occur.

• Double-blind evaluation
  Security personnel in a double-blind test have no prior knowledge of the simulated attack. They won’t have time to shore up their defences before an attempted breach, just like in the real world.

• Specific testing
  In this scenario, the tester and the security personnel collaborate and keep each other informed of their movements. This is an excellent training exercise that provides a security team with real-time feedback from the perspective of a hacker.

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