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Offensive Security Penetration Testing

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By: Cybrary Staff

December 31, 2021

How offensive security penetration testing helps uncover new threats

Having an expert well-versed in offensive security penetration testing can proactively reduce risk by uncovering vulnerabilities before attackers do.

Summary: The most dangerous cyberthreats are those carried out by skilled attackers, such as those sponsored by rival states and organized crime. Conventional security measures cannot counter these threats, hence the need for a proactive approach that intelligently manages vulnerabilities. This is where penetration testing comes in.

Conventional approaches to information security are often defensive or reactive. Data encryption, multifactor authentication (MFA), and heuristic antimalware scanning are among the many standard defensive measures. Reactive measures kick in when the usual defensive measures fail. These include malware removal solutions and other remediation methods.

While these traditional measures are just as important as they always have been, businesses are now shifting towards more proactive and even offensive approaches to cybersecurity. This trend has come about in the face of increasingly sophisticated and widespread attacks, such as highly targeted social engineering scams, organized cybercrime, and cyberwarfare.

Taking the offensive in operational information security can mean several things. One of the more controversial, not to mention legally problematic, is ‘hacking back .’ Businesses attempt to hack their adversaries to gain the upper hand. However, offensive security can also refer to offensive measures used in a defensive context. These methods include penetration testing, red teaming, and various other forms of ethical hacking.

The purpose of ethical hacking is to stay one step ahead of malicious actors through deliberate attempts to hack into an organization’s network to identify and document any vulnerabilities. These operations are carried out by Certified Ethical Hackers or Offensive Security Certified Professionals (OSCPs) working under contract with their clients, thus giving them a chance to remediate any vulnerabilities discovered before malicious actors can exploit them.

Offensive security penetration testing and similar approaches broadly consist of the following six steps:

#1. Defining the scope of the test

Before carrying out a penetration test, security leaders must first agree on the scope. This vital onboarding stage will determine how much information the client organization will share with the penetration tester. Every engagement with a penetration tester is defined by the amount of information provided, which can significantly influence the outcome.

Tests are carried out using three main categories – black box, white box, or grey box. In a black-box test, penetration testers have no information about the client’s network at all. A white box test involves sharing all network and system information with the tester, while a grey box test falls somewhere between the two.

#2. Planning and reconnaissance

The scope of the test and how much information is provided beforehand determine how the testers conduct planning and reconnaissance. This stage will be far more extensive in black box environments since the tester will not know anything about the client’s systems ahead of the analyses. This is the most authentic approach because it most accurately simulates the attack methods that real-world adversaries will use. However, it also takes significantly longer and costs more.

Penetration testers will use various tools, such as port scanners to carry out reconnaissance across the client’s network. Given enough information beforehand, the reconnaissance stage is less time-consuming and less authentic in terms of how real-world adversaries operate.

#3. Static and dynamic analyses

The next stage of the penetration test is to understand how target systems might respond to various attempts to exploit them. For example, testers may examine the application’s code to determine its behavior during routine operations. In this case, testers will use specialized hacking tools to automate the process.

A static analysis works in a non-runtime environment where testers look at the application’s code without executing it. This process is known as static application security testing or SAST. A dynamic analysis, by contrast, provides a real-time view of the application’s performance by scanning the application and its various procedure calls while it is running. This type of analysis is known as dynamic application security testing or DAST.

#4. Circumventing access controls

Equipped with a comprehensive overview of the client’s network, systems, and application code, penetration testers will then identify any potential vulnerabilities. Testers will use a range of hacking tools and methods, such as cross-site scripting attacks and SQL injections, to accomplish this.

Next, the penetration tester will try to exploit any vulnerabilities they find by circumventing the application’s access controls. This process may include escalating user privileges, exfiltrating data, or intercepting traffic. These activities gives the tester a thorough overview of the sort of damage that a real-world adversary might cause.

#5. Maintaining network access

One of the main reasons more and more organizations invest in penetration testing is to counter the rise of advanced persistent threats (APTs). A defining characteristic of an APT is its ability to gain access to a system and maintain that access over a long enough period to exfiltrate as much data as possible while remaining undetected.

This stage of a penetration test involves using the compromised system as a launchpad for a sustained attack. For example, a tester might set up network sniffers and code injection tools to compromise other connected systems and data. Trojan horses are the most common way to maintain access. Advanced ethical hackers may even create their own exploit mechanisms.

#6. Documenting vulnerabilities

The last but most important stage of a penetration test is presenting the results. These must be compiled in a comprehensive report that details the specific vulnerabilities identified, how the tester was able to exploit them, and how long they were able to remain undetected. Remediation advice may also be included.

The penetration test report and its supporting documentation allow clients the opportunity to address potential vulnerabilities and improve their information security postures. The report should be written so that less technical audiences can understand it, ideally detailing the possible consequences of exploiting a vulnerability. In addition to this report, testers should also provide a comprehensive technical overview of the methods they used.

Final words

To stop an attacker, one must think like an attacker. To that end, penetration testers use many of the same tools and methods adversaries use, albeit to help their clients or employers better understand their risk environments. Armed with this knowledge, organizations can proactively improve their security postures and, most importantly, stay one step ahead of their adversaries.

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