Penetration Testing - Basic Guide

What is Penetration Testing?

Penetration testing, also known as pen testing, simulates a cyberattack on your computer system to identify exploitable weaknesses. It often complements web application firewalls (WAFs) to strengthen web application security.

Penetration Testing Process:

A pen test follows a structured approach with distinct stages:

1. Preparation and Reconnaissance:

• Define Scope and Objectives: This involves outlining what will be tested, the attack methods to be used, and the intended goals.
• Gather Information: The tester aims to understand the target system's operation and potential vulnerabilities by collecting data like network information, domain names, and mail server details.

2. Scanning:

This stage analyzes the target application's response to various intrusion attempts:

• Static Analysis: This method involves examining the application's code to predict its behavior during operation. Tools scan the entire codebase in a single pass.
• Dynamic Analysis: This method examines the application's code while it's running, offering a more realistic view of its behavior and results.

3. Gaining Access:

This stage focuses on exploiting vulnerabilities, such as cross-site scripting (XSS), SQL injection, or backdoors, to gain access to the target system. Testers then try to escalate privileges, steal data, intercept traffic, and understand the potential impact of these vulnerabilities.

4. Maintaining Access:

This stage aims to establish a persistent presence within the compromised system, mimicking advanced persistent threats (APTs) that can remain undetected for months to steal sensitive information.

5. Analysis and Reporting:

The test results are documented in a report, outlining:

• Exploited Vulnerabilities: This details the vulnerabilities successfully leveraged by the tester.
• Accessed Sensitive Data: This includes information accessed during the test.
• Undetected Duration: This specifies the period the tester remained undetected within the system.

Security teams use this information to configure WAF settings and implement other security solutions to fix vulnerabilities and prevent future attacks.

Penetration Testing Methods:

There are various approaches to pen testing, categorized based on the tester's access and knowledge:

1. External Assessment:

This method focuses on internet-facing assets like web applications, company websites, and email and DNS servers. The objective is to gain access and potentially exfiltrate sensitive data.

2. Internal Assessment:

This simulates a malicious insider attack. The tester, with authorized access within the firewall, attempts to exploit vulnerabilities from an internal perspective. This doesn't necessarily represent a rogue employee scenario; it could also simulate an attacker who gained access through stolen credentials.

3. Blind Testing:

The tester only knows the target organization's name. This method allows security staff to observe how a real-world attack might unfold.

4. Double-Blind Testing:

Similar to a blind test, but security staff also have no prior knowledge of the simulated attack, hindering their ability to prepare defenses until the breach attempt.

5. Targeted Testing:

Both the tester and security staff collaborate and share updates throughout the process. This method serves as a valuable training exercise, providing real-time insights into attacker behavior for the security team.

Penetration Testing and Web Application Firewalls (WAFs):

Pen testing and WAFs are complementary security measures. WAF data, such as logs, can be used by the tester to identify and exploit vulnerabilities in various pen testing methods (excluding blind and double-blind tests). Conversely, pen testing results can inform WAF configuration updates to address discovered weaknesses.

Finally, pen testing fulfills compliance requirements of various security audits like PCI DSS and SOC 2. While some regulations necessitate a qualified WAF (e.g., PCI-DSS 6.6), this doesn't replace the value of pen testing in improving WAF configurations and overall security posture.

To be continued...