5 Different Types Of Penetration Testing

No one can deny the importance of dedicated cyber-security systems that keep their sensitive data safe from hackers. However, the problem is that cyber-criminals grow increasingly sophisticated in their attacks and approaches, making it imperative for organizations to stay vigilant at all times.

Lapses in security can lead to significant reputational and financial losses that can endanger the very existence of a business. That’s why companies must ensure that their clients’ data and sensitive business information are kept private and accessible only by employees who have the necessary clearance.

They must invest in a more proactive and comprehensive solution for the prevention of cyber-security breaches. Penetration testing is it.

It helps determine how safe an organization’s computer system is. Government organizations, large corporations, and banks use penetration tests to understand the vulnerabilities of their cyber-security systems. However, small companies will also find penetration testing extremely useful for their cyber-security frameworks.

What Is Penetration Testing?

Penetration tests involve cyber-security professionals attempting to break into your business’s network through any vulnerabilities they perceive. If they manage to break into the network, it’s clear that any cyber-criminal trying to do so would be successful as well.

Cyber-security professionals break into your system and target crucial information or access high-priority databases using dubious methods. This is a way to test what it’d take for a criminal to beat the security and enter the systems. It reveals the potential weaknesses of your security infrastructure and helps you stay updated with the latest engineering methods that cyber-criminals may use. This may even involve psychologically manipulating targets to extract valuable information.

You may believe that penetration testing is only valuable for large organizations and businesses, but the truth is that many cyber-criminals attack smaller companies. Since these companies often don’t have a dedicated cyber-security framework, they fall prey to the attacks, losing money and exposing valuable client data in the process.

The Ponemon Institute’s 2018 cyber-security survey found that 67% of small and medium enterprises suffered a recent cyber-attack. Only 28% believed their company’s response to vulnerabilities and attacks to be highly effective. Most of the businesses surveyed suffered exploits or malware that their cyber-security system hadn’t detected or recognized.

Penetration testers’ techniques are often much more intrusive than typical vulnerability scans and could corrupt the system, thereby hampering the entire company’s productivity. If you schedule a penetration test for your company, you could let your staff know in advance—but then you wouldn’t get to test your internal security team’s response to live threats.

To ensure your system’s safety while performing red team penetration tests, you can inform the upper-level management or blue team leader. If the situation escalates, the blue team leader will be able to control the scenario with greater awareness while still enabling the system to be tested.

It’s essential to clearly highlight your reason to the cyber-security team so they can meet your requirements. For instance, suppose you’ve rolled out a new business security plan and want to find out how effective it is. Your penetration testing team will determine whether it meets your program objectives, such as maintaining maximum availability during a cyber-attack or making sure that your data loss prevention systems (DLPs) are keeping cyber-criminals from extricating sensitive information.

By mimicking actual cyber-criminals’ behavior, cyber-security professionals can uncover critical vulnerabilities in your system and the steps you need to take to fix them. Additionally, it’s best to be aware of all the variables involved so you know which test suits your company’s specific objectives.

Why Are Penetration Tests Important?

Penetration tests are vastly more effective than typical vulnerability reports since they reveal your security team’s framework and response to real-life threats. By understanding the security issues in your network, you can remove any false positives. Using real hacking methods and patching up the problems you uncover enable you to remain confident in your cyber-security team’s ability to keep sensitive data secure.

While penetration tests are essential for safety, they’re also crucial in maintaining the company’s compliance with industrial standards of cyber-security. Organizations are legally required to comply with data protection acts such as the Federal Trade Commission Act and the California Consumer Privacy Act to keep sensitive consumer data safe.

Failure to protect and appropriately use your client data could result in reputational, financial, and legal repercussions. For example, cyber-criminals attacked the credit bureau Equifax in 2017, extricating information from three servers and stealing data bit by bit from 51 separate databases for 76 days. Equifax was forced into a global settlement that cost them $425 million. They had to pay the FTC, the Consumer Financial Protection Bureau, and all 50 U.S. states and territories for failing to keep consumer data safe.

How Often Should You Carry Out Penetration Tests?

The frequency of penetration testing depends on many factors, such as the industry your company operates in, the compliance regulations in your location, and the network technology your business uses. Penetration tests are often an essential part of industrial compliance regulations, especially in healthcare, government, and financial organizations. These industries often provide guidelines for relevant organizations to perform penetration tests to keep consumer and sensitive data safe.

Cyber-security professionals also recommend penetration testing after any of the following occurrences:

  • The application of a security patch
  • The network or cyber-security infrastructure undergoing any significant changes
  • The addition of new applications or infrastructure
  • The addition of a new office or the switch to a different office location
  • The introduction of new industry regulations that highlight additional compliance requirements
  • A spike in popularity or media attention could introduce your company to cyber-attackers’ radars.

Who Performs Penetration Tests?

Penetration tests enable you holistically view your company’s cyber-security framework. But it may be difficult for an internal employee or team member to have an objective outlook on the situation.

The majority of compliance regulations don’t require organizations to have their penetration tests conducted by third parties. However, the penetration testers must still be experienced cyber-security professionals separate from the employees who perform the network’s daily maintenance.

Therefore, many companies choose to work with third-party security experts with their own penetration testing teams. They have the expertise necessary to carry out the test and offer an unbiased, objective view of the overall security framework.

The Stages Of A Penetration Test

A standard penetration test comprises multiple steps since typical cyber-attacks also contain many different stages. Each phase aims to accomplish a particular objective that allows the attack to go further.

Step 1: Gathering Information

It all starts with research into your organization, its employees, and its cyber-security framework. Initial research avenues include the company’s website, social media presence, and your employees’ emails and social media. The testing team then decides on the resources it will use to attack your network by drawing on previous hacking occurrences and strategies.

Stage 2: Reconnaissance

The reconnaissance step involves using the initial information to gather essential details about your company from publicly available sources. This step enables the testing team to be aware of information that’s not available on your website or the notes you provide them.

The extent to which the testing team carries out reconnaissance depends on the type of test you’ve asked for. The avenues through which testers gather intelligence include tax records, internal and internet footprints, domain name queries, and tailgating.

While the exploitation stages form the core of the process, extensive reconnaissance makes penetration testing a lot faster, stealthier, and easier for the team. It’s a stage that’s often not given the importance it deserves, with many testing organizations focusing mainly on exploitation.

Stage 3: Assessing Vulnerabilities

This step involves researching your company’s network to find any open or vulnerable servers, applications, or ports that may let malware in. Scanning for vulnerabilities is the final preparatory step of penetration testing—the remainder of the stages are focused on exploitation and reporting.

Testing teams use manual and automatic methods to scan your network for vulnerabilities. These methods can be adjusted for intrusiveness and aggression since vulnerability scanning can affect your network’s stability and performance.

At this point, the testing team determines the best strategy to attack your system using the information they’ve gathered during the previous steps. They consolidate all their research to develop an exploit that exposes potential weak spots.

Stage 4: Exploitation

The testers map all the entry points and potential vulnerabilities and attempt to exploit your system. A successful exploit enables the testing team to access and control the system at a user level.

If you’ve initially outlined your objectives and the scope of the test to the cyber-security team, they’ll adhere to those guidelines. For instance, you could ask them to test only on-premise systems and avoid cloud operations altogether.

Some of the standard techniques used by ethical hackers include web applications, memory-based, network, and Wi-Fi attacks. Many teams also use social engineering methods, physical attacks, and zero-day exploits.

Stage 6: Privilege Escalation

An ethical hacker’s goal is to check the extent to which they can breach your system, recognize high-priority targets, and escape any detection methods you have in place.

After gaining access as a user, the team then exploits design flaws, bugs, and configuration errors in your system or application to move deeper into the system. The ultimate goal is to access the admin domain. The testers move further into the system using a combination of intuition, manual techniques, and automatic controls to confirm, attack, and exploit the vulnerabilities they suspect.

These techniques enable the team to obtain elevated access to data, controls, and other resources that would typically not be available to external individuals. Privilege escalation is an integral part of penetration testing since hackers use the privileges they gain through these tactics to run administrative commands, copy confidential information, and introduce malware to your system.

Stage 7: Creating Persistence

Once hackers gain access to a system, they want to maintain it for as long as possible. Cyber-criminals access different databases and steal information piece by piece through establishing persistence on the relevant network. Cyber-security professionals must be wary of advanced persistent threats (APTs) that access computer networks and manage to stay undetected for long periods. The motivators behind these stealthy threats are usually economic or political.

Ethical hackers establish their presence on your network by creating a personal login with admin access on the system as a backup and checking how long your internal cyber-security team goes without detecting them. The longer the duration, the more time cyber-criminals have to move through the attack cycle and achieve their goal.

Stage 8: Pivoting

Local traffic on networks is non-routable—attackers can’t access other computers physically connected to local networks to access its resources. This step uses pivoting techniques to enable ethical hackers to access local resources, thereby making typically non-routable traffic routable. In other words, pivoting allows attackers to configure your company’s working environment and use tools as if they were in its local network.

Stage 9: Clean-up

In this step, the ethical hacking team destroys any accounts, files, or software that they’ve used to test the system. The clean-up removes all the scripts, agents, temporary files, and executable binaries planted by the team.

The clean-up’s primary purpose is to remove all installed rootkits and backdoors, thereby returning the system’s configuration to its initial state. The team will restore all the credentials they’ve changed or removed and delete any additional usernames they created.

Stage 10: Reporting

Arguably the most crucial stage of penetration testing, reporting enables you to understand and plug in the holes in your cyber-security framework. In this stage, the testers debrief you on your pen test results.

The test report summarizes the strategy in executive terms and utilizes risk ratings to define results. This makes it easier for you to see which cyber-security issues aren’t much of a threat, as well as the steps you need to take to fix high-priority problems.

The report also comprises a detailed technical section that outlines descriptively and specifically the actions your internal team needs to take to eliminate the vulnerabilities found during penetration testing.

Additional Step: Re-Testing

While this step is optional, companies that re-test their systems ensure that the fixes they’ve utilized are successful. They also determine whether fixing the old vulnerabilities created any new risks in the system.

All the stages involved in ethically exploiting your system mimic the steps attackers typically take. However, the information you receive from a cyber-security professional depends on the kind of test and scope you’ve chosen for your system.

Types of Penetration Testing

The penetration test you choose depends on the cyber-security objectives you aim to achieve. The testing team can carry out one or a combination of these different types.

Network Testing

This type of test is the most common. Your testing team finds the cyber-security vulnerabilities in your company network’s architecture. Once the team completes extensive research on potential weaknesses, they attempt to break into the system through a series of network tests. Since hackers’ access points can be internal and external, the testing team will usually run local and remote tests to obtain the maximum amount of information possible.

Social Engineering

Social engineering tests your employees’ intuition using psychological tactics that hackers employ to steal information or introduce malware into systems. Spear phishing is one of the methods most utilized by cyber-criminals. It involves the attacker targeting organizations or individuals through email spoofing campaigns that allow them to access the victim network or steal sensitive data from it. Symantec’s 2019 Internet Security Threat Report highlighted that 65% of cyber-attack groups utilized spear phishing as their primary infection vector.

North Korean state-sponsored attacks on Israel’s defense are also an example of social engineering. Cyber-criminals used fake LinkedIn profiles to contact officials in top defense companies to gather sensitive security information.

Therefore, social engineering penetration testers use similar tactics to check how successfully they can breach your network. These tests need to be carried out both remotely and physically.

Remote Testing

Remote social engineering tests involve the pen tester attempting to manipulate your company employees into compromising their credentials or sensitive network and client information using electronic means. For instance, testers could send your employees emails as part of a spear-phishing campaign.

Physical Testing

Physical tests involve the testing team directly contacting your employees to uncover and obtain sensitive company data. Testers can impersonate your employees through phone calls, emails, or on-premise contact with personnel and devices. They may even get away with walking through the office to find computers without access controls and exploit other potential weaknesses.

Client-Side Tests

Testers attempt to exploit security gaps in local applications. If you haven’t applied new security patches or updated a network application, a hacker could quickly gain entry into your system and further their attack. The testing team will usually try to exploit holes in content creation packages and web browsing applications first.

Once an application releases a security patch, it increases your vulnerability to attack for a while since cyber-attackers become newly aware of weaknesses and try to access systems that haven’t yet applied the patch. Therefore, your internal cyber-security team must continually be vigilant and apply patches for the applications your company uses as soon as they’re released.

Web Application

This kind of penetration test is exceedingly complex and involves the testing team examining each web application your company uses for potential vulnerabilities. It takes a long time for the team to check which of your web applications could be avenues for hackers to retrieve sensitive financial and user information and how.

Wireless Network

The team uses a wireless network penetration test to examine every wireless device your organization uses. They attempt to exploit vulnerabilities and gain access to devices such as laptops, smartphones, and tablets.

The test further examines cyber-security holes in wireless access points and wireless protocols and uses these to exploit the overall network.

Hackers customize their attacks based on the technology and type of system you use; penetration testers do their job in the same way. The attacks are specific to your company, employees, and cyber-security protocols, thereby enabling you to have a holistic overview of your system’s safety.

Penetration Testing vs. Risk Assessment

The terms that define cyber-security tests and scans are often used interchangeably. You may be confused between a penetration test, risk assessment, and vulnerability scan for your company. However, these different scans and assessments hold unique, separate purposes.

Risk Assessment

A risk assessment involves building a custom blueprint of your company’s cyber-security framework, the strategies to improve your security posture and eliminate the risks found. Risk assessments typically use network research, vulnerability scans. The information enables you to mitigate risks and stay within organizational budgets.

Risk assessments don’t equip you with an understanding of potential attacks your organization is vulnerable to since it only uses known network weaknesses. After a risk assessment, your network could still be exposed to multiple threats that you do not know about.

Penetration Testing

Penetration tests exploit known weaknesses in your company’s network and go a step further by uncovering and exploiting additional vulnerabilities that don’t typically show up on scans. While risk assessments can provide valuable insight into your security posture, a penetration test is the best way to discover your system’s vulnerabilities.

A thorough penetration test gives you a full view of the cyber-security measures your company needs to take. The testing team may inform you that your employees need to be better educated on cyber-security protocols or that attackers can easily establish a presence on your network. Penetration testing is so effective since it relies on human intuition in addition to technological tactics of exploitation.

It’s best to conduct thorough research on the service you’re purchasing. Risk assessments and penetration tests are both critical for your organization’s network to be secure, but their objectives are different. Before buying a test or assessment, ask yourself what you need to achieve and consider the industrial compliance regulations, current security protocols, and size of your company. All of these factors play a role in the service you need.

White Box vs. Black Box Penetration Tests

Cyber-security professionals will ask you whether you need a white box or a black-box test to determine your system’s potential vulnerabilities. Here’s how they’re different.

White Box Penetration Tests

A white box penetration test equips the testers with information about your company network’s architecture, thereby enabling them to levy faster, more aggressive customized attacks at your system. It’s a thorough method that expands the penetration testing area. Still, its drawback is that it’s not often very realistic since testers have more information to go on than potential hackers typically would.

Black Box Penetration Tests

Alternatively, black-box penetration tests don’t provide the tester any information about your organization’s security posture and internal functioning. The tester has to rely on base knowledge and intuition to exploit your system. It’s a spontaneous network test that gives the target no warning, thereby allowing it to be incredibly realistic.

Why Your Company Should Invest In Penetration Testing

Penetration testing and its subsequent reporting are valuable tools for your organization’s cyber-security posture. You can find system vulnerabilities and patch them up, but that’s not the only reason companies use these tests. Here are all the different reasons companies invest in penetration tests.

Finding Critical Vulnerabilities Before Attackers Do

Penetration tests go beyond regular risk assessments since they attempt to exploit both known and potential weaknesses in your system before cyber-criminals do. For instance, while other scans and assessments could inform you about the patches you need to apply, a penetration test will highlight risks and vulnerabilities by using the tactics that a persistent cyber-criminal will use.

Team Training

Social engineering penetration tests enable you to determine where your employees fall short in cyber-security awareness and protocol. For example, suppose the testing team carries out a successful phishing attack. In that case, you could hold a workshop for your employees to educate them on how they can avoid similar breaches in the future.

Faster, Streamlined Security Response

A penetration test enables you to understand what areas of your cyber-security training or technology need to improve. The report will equip you with a detailed summary of potential vulnerabilities and the steps you can take to improve your security posture. You can eliminate these weaknesses by giving high-risk vulnerabilities the most priority.

Maintaining Compliance

Healthcare, government, legal, IT, and financial organizations all have to comply with industrial regulations, which sometimes highlight penetration tests as a requirement. For instance, the PCI DSS (Payment Card Industry Data Security Standard) requires companies that handle customers’ card information to perform penetration tests at least once a year or after significant changes to their system. These changes include—but aren’t limited to—the installation of new components in the system, major infrastructure modifications, and application upgrades.

Protect Your Organization’s Reputation

An exposed system can provide quick and undetected entry through vulnerable access points for hackers to steal sensitive client and company information. Whether cyber-attackers steal customer or client data, you stand at risk for loss of public favor.

A penetration test enables you to avoid the financial and reputational losses attached to cyber-security breaches. It mimics real-life hacking scenarios to check whether the testing team can successfully breach your system and how long they manage to stay undetected by your internal cyber-security employees.

Improve Your Cyber-Security Posture With Penetration Testing

Penetration testing is an incredible learning opportunity for you and your cyber-security team. You’ll be aware of vulnerabilities long before anyone can exploit them to access your system.

Once a penetration test is complete, you can use the results to streamline your entire company’s cyber-security protocol and responses. The penetration testing report equips your company with the knowledge of high-priority risks and the responses you need to take to fix these vulnerabilities. Penetration tests are also an ideal way for you to show your clients that your organization values security.