The escalating threat of hackers grows more serious each day. A TechRepublic survey of more than 400 IT security professionals found that 71% of them had seen an increase in security threats or attacks since the start of the COVID-19 outbreak. Should a hacker successfully breach your defenses, the damages—to your reputation, bottom line, and operational capabilities—could be catastrophic.To gauge your cybersecurity defenses and spot vulnerabilities in your critical IT systems, you need to consider different types of penetration testing.
What are penetration tests? And which one is needed for your company?
What is a Penetration Test?
A penetration test, also referred to as a pen test, typically involves a team of security professionals, working to penetrate your company’s networks or servers. They accomplish this by identifying vulnerabilities and then exploiting them. Because of this, pen tests are frequently referred to as a type of ethical hacking.
Pen tests are an effective defense mechanism because they mimic real-world attacks. They allow you to see the weak points in your cybersecurity perimeter—whether that be backdoors in the OS, unintentional design flaws in the code, or improper software configurations.
Benefits of conducting tests on a periodic basis include:
- Reveals exposures in your application configurations and network infrastructure
- Protects IP as well as sensitive and private data
- Highlights real risks of an actual hacker successfully breaching your defenses
- Measures your cyberdefense capabilities—your ability to detect attacks and then respond in a timely manner
- Ensures that your network and operations are running smoothly 24/7 and don’t suffer unexpected down time
- Maintains compliance with regulations and certifications such as PCI or ISO
- Provides an objective 3rd party opinion on the efficacy of your cybersecurity efforts
Penetration tests are designed to be intense and invasive. The goal is to test the entirety of your perimeter to get as much actionable information as possible. Per SC Magazine
Penetration testing can be conducted on hardware, software, or firmware components and may apply physical and technical security controls. It often follows a sequence of a preliminary analysis based on the target system, then a pretest identification of potential vulnerabilities based on previous analyses. Once that is complete, a pretest may help determine the exploitation of the identified vulnerabilities.
Both parties must agree to the set of rules prior to launching tests. Then, the tests need to be applied to your whole network.
The Three Forms of Penetration Tests
There are three primary ways to conduct a penetration test:
- Black-box test
- White-box test
- Gray-box test
Black-box testing, also known as external penetration testing, simulates an attack from outside of your organization.
The pen tester starts off on the same footing that a real hacker would. This means they begin with little to no information about the IT infrastructure and security defenses. They don’t know the internal workings of:
- The web applications
- The software architecture
- The source code
This form of testing gives you an idea of what an outsider would need to do to breach your defenses. But the test doesn’t just end at that point. There’s more to learn. A tester also wants to see how much damage they could possibly inflict once they’re in the system. According to Infosec Institute:
Black-box penetration testing relies on dynamic analysis of currently running programs and systems within the target network. A black-box penetration tester must be familiar with automated scanning tools and methodologies for manual penetration testing. Black-box penetration testers also need to be capable of creating their own map of a target network based on their observations since no such diagram is provided to them.
Typically, a tester goes from the internet into the router, seeking to bypass the firewall defenses. This is accomplished by launching an all-out, brute force attack against the IT infrastructure. It performs a sort of trial and error approach, wherein automated processes indiscriminately search for exploitable vulnerabilities.
A black-box test can take up to six weeks to thoroughly complete, although it could go even longer depending on the scope of the project and the rigor of testing.
Sometimes referred to as clear box testing or internal testing, this type of pen test gives the tester access to source code and the software architecture from the outset. It mimics an attack from an employee or hacker who’s already gained access to the system.
The pen tester begins with the same privileges that an authorized user would have. From there, they try to exploit system-level security and configuration weaknesses. The goal of this test is to perform an in-depth audit of the various systems and answer two key questions:
- How deep could an attacker go via privilege escalation?
- How much damage could an attack cause?
An internal test can take two to three weeks to finish.
Gray-Box Penetration Testing
As the name implies, gray-box testing is the middle ground between an internal and an external test. The tester is simulating an attack from the outside, except in this case, the hacker has the partial knowledge levels of a user.
It’s purpose is to search for defects in the code structure or application, using a blend of white-box and black-box methodologies. The hybrid test measures user inputs to see what outputs the software produces in response. Generally, the test will be conducted via a combination of manual processes and automated programs.
Common scenarios that a gray-box test is meant for include:
- The hacker has user or admin accounts that they can login with
- The hacker has a deep understanding of the application’s data flow and architecture
- The hacker has access to parts of the source code
Because it uses a mixture of both methodologies, some consider it to be the best ROI for your time and resources. It delivers many of the benefits of both an internal and external test. That said, a gray-box test only provides limited coverage of the application and source code. To make matters more complicated the tests aren’t easy to design.
The 5 Types of Pen Testing
Now that we’ve covered the primary ways a penetration test can be performed, it’s possible to dive into the most common types of tests. Most of them will utilize a combination of white-box and black-box testing methodologies. They include:
Network Service Penetration Testing
A network penetration test is used to identify exploitable weaknesses within your:
- Network devices
Your mission is to find and then close them before a hacker can take advantage. When done correctly, it can demonstrate the real-world vulnerabilities that a hacker might be able to leverage to gain access to sensitive data or take control of the system. The discovery process allows your team to find better ways to protect private data and prevent system takeovers.
What does it entail?
Most penetration tests will follow the 7 steps of the Penetration Testing Execution Standard (PTES):
- Pre-engagement interactions – The internal team and security partner meet to discuss and define the engagement scope.
- Intelligence gathering – The testers seek to discover all accessible systems and their various services in order to get as much information as possible.
- Threat modeling – The tester identifies exploitable vulnerabilities within the system, via manual testing and automated scanning.
- Vulnerability analysis – The tester documents and analyzes the most glaring vulnerabilities in order to formulate a plan of attack.
- Exploitation – The tester actually performs tests in an attempt to exploit vulnerabilities.
- Post exploitation – The tester tries to determine the value of the machine compromised and to maintain control of it so it can be used at a later point.
- Reporting – The tester compiles findings, ranking and prioritizing vulnerabilities, providing evidence, and recommending responsive measures.
Web Application Penetration Testing
The expansion of web applications has made it so that greater internet resources must be spent on developing software and configuring the applications to work properly. But this also represents a significant new attack vector for hackers, particularly since some web applications can hold sensitive data.
Web application penetration testing seeks to gather information about the target system, find vulnerabilities, and then exploit them. The end goal is to completely compromise the web application.
This is also known as Web Application Penetration Testing (WAPT). It’s capable of testing for the following scenarios:
- Cross Site Scripting
- SQL Injection
- Broken authentication and session management
- File Upload flaws
- Caching Servers Attacks
- Security Misconfigurations
- Cross-Site Request Forgery
- Password Cracking
Often viewed as a “deeper dive” test, a WAPT is much more thorough and detailed, particularly when it comes identifying vulnerabilities or weaknesses in web-based applications. As a result, a significant amount of time and resources must be devoted to adequately test the entirety of a web application.
Wireless Penetration Testing
Wireless penetration testing aims to identify and then gauge the connections between all devices connected to your business wifi network, including:
- Mobile devices
- IoT devices
The test is conducted on-site since the pen tester must be in range of the wireless network to access it. And the goal of the test is relatively straightforward: find the vulnerabilities in the wifi access points.
What are the steps involved?
- Wireless reconnaissance – Information is gathered via wardriving—which involves driving around the physical location to see if the wifi signals pop up.
- Identify wireless networks – Tester scans and identifies wireless networks using packet capture and wireless card monitoring.
- Vulnerability research – After the tester finds wifi access points, they try to identify vulnerabilities on that access point.
- Exploitation – The tester attempts to exploit the vulnerabilities in one of three ways:
- De-authenticating a legitimate client
- Capturing an initial 4-way handshake
- Running an offline dictionary attack on a capture key
- Reporting – The tester documents every step of the process, including detailed findings and mitigation recommendations.
Social Engineering Penetration Testing
The most significant security risk to your organization—bar none—are your employees. According to Security Magazine:
Cybercriminals are aggressively targeting people because sending fraudulent emails, stealing credentials, and uploading malicious attachments to cloud applications is easier and far more profitable than creating an expensive, time-consuming exploit that has a high probability of failure. More than 99 percent of cyberattacks rely on human interaction to work—making individual users the last line of defense.
If your attempt to improve your security doesn’t include your employees, then all of your efforts will be in vain. They should be your chiefmost concern.
With a social engineering penetration test, the tester attempts to persuade or fool employees into providing sensitive information, such as a username or password.
There are a variety of social engineering penetration attacks, including:
- USB drops
- Watering hole
- Whaling attack
- Quid pro quo attack
- Dumperster diving
Improving employee awareness and providing training on common social engineering attacks is one of the very best ways you can prevent an attack from occurring or being successful.
Physical Penetration Testing
A physical penetration test simulates the old-school way to breach security.
The pen tester attempts to get past the physical security barriers and gain access to your business’ security infrastructure, buildings, or systems. It tests the various physical controls you have in place, including:
- Security guards
Although this is often viewed as an afterthought, if a hacker is able physically bypass your security and then access the server room, they could easily gain control of your network. So, it’s critical that your physical security posture is just rigorously protected as your cybersecurity perimeter.
RSI Security – The Pen Testing Experts
Pen testing is one of the very best ways that you can measure the effectiveness of your cybersecurity and physical security. Whether you use white-box, black-box, or gray-box methodologies, each pen test seeks to simulate a real-world attack—just without the consequences.
Today, there are five essential types of penetration testing, including:
- Network service
- Web application
- Social engineering
By performing all of these tests on a periodic basis, you can ensure that your cyberdefenses are sound.
But who can you rely on to adequately perform these various tests?
RSI Security is the penetration testing services expert. Thanks to our decades of experience, we know exactly what it takes to assess your cybersecurity defenses and then address your glaring weaknesses.
Are you ready to get started? So are we.