What Is Penetration Testing? Types and Techniques

Security should be a multi-layered approach. One of those critical layers is Penetration Testing.

Is your data safe in today’s rapidly changing world of cybersecurity attacks?

The best way to find out if application systems are secure is to attempt to hack them yourself. A tried and tested method is a penetration test, a form of application scanning. Vulnerability detection aims to identify potential weakness before the bad guys do

In this article, we will discuss what pen testing is, different types, and how your organization can benefit from it.

By definition, penetration testing is a method for testing a web application, network, or computer system to identify security vulnerabilities that could be exploited. The primary objective for security as a whole is to prevent unauthorized parties from accessing, changing, or exploiting a network or system. It aims to do what a bad actor would do.

Consider a Pen Test an authorized simulation of a real-world attack on a system, application, or network to evaluate the security of the system. The goal is to figure out whether a target is susceptible to an attack. Testing can determine if the current defense systems are sufficient, and if not, which defenses were defeated.

These tests are designed to target either known vulnerabilities or common patterns which occur across applications — finding not only software defects but also weaknesses in network configurations.

A pen-test attempts to break a security system. If a system has sufficient defenses, alarms will be triggered during the test. If not, the system is considered compromised. Penetration testing tools are used to monitor and improve information security programs.

Though system administrators need to know the difference between a test and an actual threat, it’s important to treat each inspection as a real-world situation. Though unlikely, credible security threats could occur during the test.

Penetration tests are often creative rather than systematic. For example, instead of a brute force attack of a network, a pen-test could be designed to infiltrate a company executive via his/her e-mail. Approaching the problem creatively as an infiltrator is more realistic with what could potentially be a real attack someday.

Once a test is complete, the InfoSec team(s) need to perform detailed triage to eliminate vulnerabilities or defer action where a weakness poses little or no threat.

Typically, penetration testers are external contractors hired by organizations. Many organizations also offer bounty programs. They invite freelance testers to hack their external-facing systems, such as public websites, in a controlled environment with the promise of a fee (or other forms of compensation) to breach an organization’s computer systems.

There is a good reason why organizations prefer to hire external security professionals. Those who do not know how an application was developed may have a better chance of discovering bugs the original developers may never have considered or maybe blind toward.

Penetration testers come from a variety of backgrounds. Sometimes these backgrounds are similar to those of software developers. They can have various forms of computer degrees (including advanced ones), and they can also have specialized training in penetration security testing. Other penetration testers have no relevant formal education, but they have become adept at discovering security vulnerabilities in computer software. Still, other penetration testers were once criminal hackers, who are now using their advanced skills to help organizations instead of hurting them.

Before explaining the different methods for a penetration test, it’s necessary to understand the process of gathering intelligence from systems and networks.

Intelligence gathering, or Open Source Intelligence (OSINT) gathering, is a crucial skill for testers. During this initial phase, ethical hackers or cybersecurity personnel learn how the environment of a system functions, gathering as much information as possible about the system before beginning.

This phase will usually uncover surface-level vulnerabilities.

It includes a scan of:

• The local and wireless network
• Pertinent applications
• Website
• Cloud-based systems
• Employees
• Physical hardware facilities

After gathering intelligence, cybersecurity professionals move on to threat modeling.

Threat modeling is a structured representation of the information that affects system security. Security teams use this type of model to treat every application or feature as if it were a direct safety.

Threat modeling captures, organizes, and analyzes the bulk of intelligence gathered in the previous preparation phase for a penetration test. It then makes informed decisions about cybersecurity while prioritizing a comprehensive list of security improvements, including concepts, requirements, design, and rapid implementation.

Threat modeling is a process of its own, and can be summed up by asking the following four questions:

1. What are we working on?
2. What can go wrong with what we’re working on?
3. What can we do to ensure that doesn’t happen?
4. Did we completely eradicate the problem?

There is no single, right way to investigate vulnerabilities in a system. But combinations of these questions can go a long way toward finding solutions.

Cybersecurity professionals define and identify vulnerability assessment scope, threat agents, existing countermeasures, exploitable vulnerabilities, prioritized risks, and possible countermeasures during threat modeling.

Following intelligence gathering and threat modeling, a penetration test itself is the next process.

Below are various penetration testing methodologies. It’s important to test for as many potential weaknesses throughout your system and network as possible.

Conducting multiple tests can reveal more vulnerabilities and provide your security and IT teams with more opportunities to address and eliminate security threats.

This type of test includes both internal and external network exploitation testing through the emulation of hacker techniques that penetrate a system’s network defenses. Once the network has been compromised, the tester can potentially gain access to the internal security credentials of an organization and its operation.

Testing of a network includes identifying:

• Threat Modeling
• Vulnerability Scanning & Analysis
• Firewall bypassing
• Router and proxy server testing
• IPS and DPS evasion
• Open port scanning
• SSH security attacks

Network testing is more in-depth than standard penetration testing and locates vulnerabilities that basic scans may not find, all to create a safer overall network.

Application security tests search for server-side application vulnerabilities. The penetration test is designed to evaluate the potential risks associated with these vulnerabilities through web applications, web services, mobile applications, and secure code review.

The most commonly reviewed applications are web apps, languages, APIs, connections, frameworks, systems, and mobile apps.

Wireless and website tests inspect relevant devices and infrastructures for vulnerabilities that may compromise and exploit the wireless network.

Recently, Mathy Vanhoef, a security expert at the Belgian University KU Leuven, determined that all WiFi networks are vulnerable to hacking through their WPA2 protocols.

This exploit can reveal all encrypted information, including credit card numbers, passwords, chat messages, emails, and images. Injection and manipulation of data are also possible, leading to the potential for ransomware or malware attacks that could threaten the entire system.

To prevent wireless network hacking, check for the following during pen testing:

• webserver misconfiguration including the use of default passwords
• malware and DDoS attacks
• SQL injections
• MAC address spoofing
• media player  or content creation software testing vulnerabilities
• cross-site scripting
• unauthorized hotspots and access points
• wireless network traffic
• encryption protocols

Social engineering tests search for vulnerabilities an organization could be exposed to based on its employees directly. In this case, creative testing must be designed to mimic real-world situations that employees could run into without realizing they’re being exploited.

These tests not only help with internal security strategy amongst co-workers but allow security teams to determine necessary next steps in cybersecurity.

Specific topics such as eavesdropping, tailgating, or phishing attacks; posing as employees; posing as vendors/contractors; name-dropping or pretexting; gifts or dumpster diving; bluesnarfing; quid pro quo; or baiting, are common testing practices.

Bad actors typically possess social engineering skills and can influence employees to create access to systems or sensitive customer data. When used in conjunction with other physical tests, social engineering testing can help to develop a culture of security throughout an organization.

Physical penetration testing prevents hackers from gaining tangible access to systems and servers by ensuring that facilities are impenetrable by unauthorized personnel. IT and cybersecurity professionals focus primarily on system vulnerabilities and may overlook physical security aspects that can result in exploitation. Physical penetration tests focus on attempts to access facilities and hardware through RFID systems, door entry systems and keypads, employee or vendor impersonation, and evasion of motion and light sensors.

Physical tests are used in combination with social engineering such as manipulation and deceit of facility employees to gain system access.

In a Computer Network Exploitation (CNE), networks can be used to target other systems directly.

For example, attempting to extract and obtain sensitive information and data such as classified intelligence or government documents. This type of attack is commonly performed within government agencies and military organizations and is considered surveillance, wiretapping, or even cyber-terrorism.

In a Computer Network Attacks (CNAs), the goal is to destroy or corrupt information that exists on a victim’s network through an Electronic Attack (EA). EA’s can use techniques such as an electromagnetic pulse (EMP) designed to incapacitate a network or system.

Types of CNAs can overlap with social engineering and include data modification and IP address spoofing; password-based attacks; DDOS; Man in the middle attacks; or compromised key, sniffer, and application layer attacks.

Cloud services are essential for group collaboration, networking, and storage. Large amounts of data are stored within the cloud, which means that it is a hotbed for hackers seeking to exploit this technology.

Cloud deployment is relatively simple. However, cloud providers often have a shared or hands-off approach to cybersecurity, and organizations are responsible for vulnerabilities testing or hacking prevention themselves.

Cloud penetration testing is a complicated test, but one that is necessary and important.

Typical cloud testing areas include:

• Weak passwords
• Network Firewalls
• RDP and SSH remote administration
• Applications and encryption
• API, database, and storage access; VMs; and unpatched operating systems.

Public cloud penetration testing can be among the most complicated to perform.

Utilize a “white box” method of testing by making use of as much information as possible about the target system. This includes the software it runs, and the network architecture, source code.

This will ensure you have the intelligence to accomplish the test. Be aware that public cloud services providers limit your penetration testing abilities due to the resource limitations of shared infrastructures.

For instance, Amazon Web Services (AWS) requires that you fill out the AWS Vulnerability Testing Request Form before testing and forbids certain types of pen tests.

Microsoft Azure lists its Microsoft Cloud Unified Penetration Testing Rules of Engagement on its website.

On-premises subscribers and cybersecurity personnel can scan applications, data, runtime, operating system, virtualization, servers, storage, and networking.

In the cloud, they can test applications, data, runtime, and operating systems for IaaS; applications and data only for PaaS; and no subscriber testing for SaaS.

Cybersecurity is a concern for all businesses. Constant threats to IT systems and networks are non-stop. Identifying weaknesses thru testing can prevent unauthorized parties from accessing data. Ensure that your applications and network systems have an evolving multi-stage security approach.

Designing tests that simulate attacks on hardware, software, networks, and even your employees, you can quickly determine the weaknesses.