Advanced Penetration Testing Techniques: Beyond the Basics

Advanced penetration testing involves security engineers simulating planned attacks against an organization's security infrastructure.

20:23 03 September 2024

As a more comprehensive approach than vulnerability assessments alone, penetration testing has become an increasingly crucial part of a holistic security strategy, given the growing imperative to harden defenses around digital infrastructure, sensitive data, and business operations.

Advanced penetration testing involves security engineers simulating planned attacks against an organization's security infrastructure to uncover risky misconfiguration and critical vulnerabilities that need to be patched.

Security professionals are constantly in demand for this very reason, and to stay ahead of the curve, they must keep abreast of the latest technologies, including advanced penetration testing techniques.

Consider it like a high-security facility hiring a team of experts to simulate a breach, attempting to infiltrate their physical premises and bypass security systems. If the 'red team' succeeds, the facility gains critical knowledge on how to improve their physical security measures.

Let's take a closer look at the advanced stages of penetration testing that help expose vulnerabilities often missed by basic security checks.

The Advanced Penetration Testing Techniques

Before a penetration test begins, the security testing team and the company establish a scope for the engagement. This scope will delineate which systems will be tested, the timeframe for the testing, and the methods the testers are authorized to use. The scope also determines the level of information the testers will have access to in advance.

Blind Test

Imagine you're the chief information security officer for a major healthcare provider that's developing a groundbreaking new electronic health records system. You've received intelligence suggesting that cybercriminals are targeting healthcare organizations with similar initiatives. To ensure the system's security before it goes live, you could conduct a blind penetration test.

A blind test gives security testers only the name of the company they're targeting. This lets them see what a real attack on that company's software would look like and how well the company's defenses would hold up.

Blind testing is especially useful during the development phase of new software. Because developers need to see how the software handles different situations without giving away which tests were done. This way, if they find a bug, they can fix it without spilling the beans on what they were testing.

⁤And it is even more useful for security assessments when checking how secure a company's systems are. ⁤⁤By not knowing which parts are being tested, the security team gains a real-world view of what an attack might look like. ⁤⁤This helps them make smarter choices about how to protect the company from future threats.

Double-Blind Test

Double-blind tests are valuable because they help security teams be better prepared for actual attacks, as they've seen how things might play out in a realistic scenario. Even the company's security team doesn't know an attack is happening, so there's no chance to quickly fix things before the attack hits.

The results show how well the company's defenses actually work and what needs improvement. They can also highlight weak spots and where more training is needed.

Here's how it works: security experts create a file that looks like a real virus, complete with digital signatures and behaviors that mimic known malware. They then discreetly introduce this file into the company's network, perhaps through an email attachment or a seemingly harmless download link. Unsuspecting security analysts, believing this to be a genuine threat, will analyze the file and try to determine its origins and potential impact.

The entire process is monitored, allowing the experts to observe how the security team responds, the tools and techniques they use, and the time it would take to identify and neutralize the "threat." This provides invaluable insights into the effectiveness of the company's incident response procedures, the strengths and weaknesses of their security posture, and the overall preparedness of their personnel.

Black-Box Testing

In a black-box test, security testers know nothing about the system they're trying to break into. They have to figure it out like a real hacker would, doing their own research to plan an attack.

Black-box testing focuses on a company's internet-exposed assets that anyone can see, like their website or public servers. And threat actors can use these to devise an attack plan to get your data or mess with your systems.

One thing malicious attackers typically do is reconnaissance: they check out things like Google Street View to map out a company's buildings and look for weak spots. They might also use information from past hacks, like leaked passwords. Once they find a target, they try to exploit and take advantage of any weaknesses they find.

The most common attacks in black-box testing include things like SQL injections, buffer overflows, and cross-site scripting, since attackers can exploit these vulnerabilities to gain access to sensitive data or systems.

Black-box testing is essential to ensure that your company's assets are protected from attack. By testing and trying to exploit weaknesses, testers can identify and help fix any security issues before an attacker can exploit them.

White-Box Testing

White box testing is a type of application security assessment that provides the tester with complete knowledge of the application, including access to source code and design documents.

Security testers get full access to the inner workings of the system they're checking out. The company shares everything—network diagrams, source codes, passwords, the whole shebang.

This in-depth visibility makes it possible for white box testing to identify issues that are invisible to gray and black box testing.

White-box testing gives developers a clear picture of how their software acts normally, and when it's faced with unexpected or harmful actions. This information helps them fix problems before they get out of hand and keeps users safe from potential threats.

There are a number of tools and tricks for white-box testing. One popular way is to test how the software actually works by running specific commands or scripts within it. Another is to watch for weird or unexpected behavior, which can alert developers when something's wrong.

Gray-Box Testing

Gray-box testing is a less invasive alternative to traditional methods and is effective for evaluating a broad spectrum of security features and vulnerabilities. It usually involves various tools and techniques, such as web browsers, network probes, vulnerability scanners, and intrusion detection systems.

Gray-box tests can be executed on either live systems or simulated environments. Security testers are provided with partial information about the target system, such as IP ranges for network devices, but must independently probe for vulnerabilities.

This approach is a practical way to assess the security posture of an IT infrastructure, allowing testers to simulate realistic attacks while maintaining some control over the testing environment and data. Organizations often adopt the gray-box testing method to evaluate their security posture before employing more invasive techniques.

Staying Ahead of the Threats

Threat hunting is a proactive method for uncovering previously unknown or ongoing non-remediated threats within an organization's applications. Siemba provides access to their global team of ethical hackers, who are hired to identify and address vulnerabilities that attackers could exploit for personal gain.

Regardless of the specific technique used, security testing teams typically follow established penetration testing methodologies to ensure a thorough and systematic assessment. Siemba offers a penetration testing as a service (PTaaS) platform for your applications, with advanced test automation capabilities to help uncover and fix security vulnerabilities that could expose your most important assets to an attack.

Siemba's offensive security solutions help you secure your technology stack and customer-facing assets, safeguarding against data breaches and cyberattacks. Don't wait for a breach — get in touch for expert security guidance.