Penetration Testing: A Complete Guide

A Comprehensive Guide to Penetration Testing

To keep your digital assets and networks secure, you must stay one step ahead of the game. One way to do this is through penetration testing. This article will explore the different types of penetration testing, their benefits, the process, and tips for selecting a provider.

What is Penetration Testing?

Penetration testing, also known as “pen testing,” is essential to an organization’s cybersecurity strategy. It is a proactive security approach used to evaluate the security strength of an organization’s network, systems, and applications. Penetration testing involves a simulated cyber-attack on a system to detect and identify any security vulnerabilities that cybercriminals can exploit. The goal is to address any weaknesses or gaps in your cybersecurity posture before an attack occurs.

Benefits of Penetration Testing

1. Pinpoint Vulnerabilities

Penetration testing identifies existing system or application configurations and network infrastructure weaknesses. Penetration tests also reveal employee activities that could lead to data breaches and malicious infiltration. A detailed report will identify which software and hardware improvements to consider and provide recommendations and policies to improve your overall security posture.

2. Improve Regulatory Compliance  

Penetration testing helps ensure your organization complies with industry standards and regulations such as PCIHIPAAFISMA, and ISO 27001. In addition, regularly performing these tests helps to demonstrate due diligence and your dedication to security, all the while helping you to avoid the costly fines associated with non-compliance.

3. Test Your Cyber Defense Resilience

Penetration testing helps validate your existing cybersecurity controls, identify misconfigurations and areas of improvement, and test your remediation capabilities. 

4. Ensure Business Continuity

Penetration testing is a proactive approach to cybersecurity and will help you avoid or at least minimize the impact of cyber threats. As a result, you ensure maximum uptime and productivity for your business.

5. Maintain Stakeholder Trust

A cyber attack or data breach negatively affects the confidence and loyalty of your customers, suppliers and partners. However, if your company is known for its comprehensive security strategy, including penetration tests, it will help reassure your stakeholders.

Approaches to Penetration Testing

Penetration tests differ both in their approach and in the weaknesses they attempt to exploit. The level of information the pen tester receives determines their approach as well as the scope of the project.

Black Box Testing

Black box testing is a type of penetration testing that focuses on the external aspects of a system. The pen tester assumes the role of a typical hacker with no internal knowledge of the system, such as source code or architecture. This test determines the vulnerabilities in a system that are exploitable from outside the network. It is considered the most authentic as it demonstrates how an attacker with no inside knowledge would target and compromise an organization. 

White Box Testing

White box testing, sometimes called crystal or oblique box pen testing, is when the pen tester has full knowledge and access to the source code and environment, including network maps and credentials. A white box penetration test helps simulate a targeted attack on a specific system utilizing as many attack vectors as possible.

Grey Box Testing

During a gray box penetration test, the pen tester has partial knowledge or access to an internal network or web application, usually in the form of login credentials. As a result, grey box testing helps organizations understand the level of access a privileged user could gain and the potential damage they could cause.

Types of Penetration Testing

Penetration testing can be divided into several different types. Each type offers various benefits and is suited for different kinds of organizations. Here are some of the most common types of penetration testing:

Network Penetration Testing

Network penetration testing is one of the most common types of penetration testing. The primary purpose is to identify and address potential weaknesses in the system’s network infrastructure, such as servers, routers, switches, firewalls, and VPNs.

Web Application Penetration Testing

Web application penetration testing exploits vulnerabilities or security weaknesses in web-based applications, browsers, and their components such as ActiveX, Plugins, Silverlight, Scriptlets, and Applets. The most common vulnerabilities to look for in a web application penetration test include the following:

  • Unprotected access points
  • Weak passwords
  • SQL injection attacks
  • Code injection
  • Cross-site scripting
  • Data breach
  • Phishing attacks

Client-Side Penetration Testing

Client-side penetration testing, also known as internal testing, aims to exploit vulnerabilities in client-side application programs such as email clients, web browsers, media players, open-source apps and programs such as Adobe Photoshop and the Microsoft Office Suite. Apart from third-party apps, it may also include internal programs and frameworks.

Wireless Penetration Testing

Wireless penetration testing aims to identify vulnerabilities on any physical wireless device connected to the WiFi network, such as laptops, tablets, smartphones, etc. It includes looking for encryption weaknesses, vulnerabilities in wireless protocols, wireless access points, admin credentials, default or weak passwords, unauthorized hotspots and denial of Service (DoS) attacks.

Social-Engineering Penetration Testing

A social engineering penetration test helps determine how susceptible your employees are to social engineering attacks such as phishing attacks, tailgating, scareware, pretexting, smishing, name-dropping etc. The pen testing organization may also provide security awareness training to help educate and inform employees on the most current cyber attacks and how to avoid them.

Physical Penetration Testing

Physical security is equally essential as digital security when it comes to improving your overall security posture. During a physical penetration test, the tester will try to circumvent the physical security barriers of your organization, such as locks, sensors, fences, security guards, cameras, etc., to access restricted areas, identify sensitive information, and gain a foothold on the network.

6 Phases of Penetration Testing 

The penetration testing process involves several steps, including planning, reconnaissance, scanning, exploitation, and reporting.

1. Create a Comprehensive Plan 

Your plan should outline the reasons for conducting pen testing, list high-priority and low-priority areas, identify resourcing requirements, establish and define liabilities, determine the testing to be undertaken and discuss follow-up activities.

2. Reconnaissance

In this phase, the pen tester collects as much information about the target system as possible, including details about network components, operating systems, open ports, applications, access points, and potential attack vectors. The tester must gather as much data as possible to plan an attack strategy effectively.

3. Scanning

In this phase, testers look for entry points. It involves using automated tools to scan the system for potential vulnerabilities an attacker could exploit. Various scanners may be used, such as war dialers (computer programs used to identify phone numbers), port scanners, network mappers (used for network discovery and security auditing), and vulnerability scanners (identifies problems in the system).

4. Gaining Access

Now that the pen tester understands the scope and testing components, they will simulate an attack in a controlled environment. For example, mimicking a real-world bad actor, the tester may take control of a device to extract sensitive data; perform a Denial-of-Service (DoS) attack or web application attack, such as cross-site scripting or SQL injection; or perform a physical attack. 

5. Maintaining Access 

In this stage, the goal is to see if the tester can use the vulnerability to expand their access and maintain their presence for as long as possible. For example, the pen tester may try to expand their permissions, find user data, and remain stealthy while running their programs deeper into the IT infrastructure.

6. Reporting

Reporting is a critical component of any penetration test. It involves creating comprehensive documentation of the penetration results, including exploited vulnerabilities, sensitive data that was accessed, and the amount of time the pen tester remained undetected. It also includes clean-up activities, remediation advice, and strategic recommendations for improving security posture. 

Tips for Hiring a Penetration Testing Expert

To overcome the cybersecurity skills shortage, partnering with a reputable managed service provider (MSP) for penetration testing is a cost-effective and efficient option. Outsourcing pen testing to certified experts gives you access to the security resources and expertise you might not have in-house. Before you hire a managed service provider, here are some key considerations:

1. Expertise

When you decide to outsource pen testing, the provider you choose should exude expertise and experience. Certifications, licenses, and accreditations are all excellent indicators of a pen tester provider’s abilities to conduct tailored tests that will meet your needs and goals and advise you on the different testing options.

2. Reputation

If you only look at an MSP’s certifications and qualifications, you might not be able to get a sense of their professionalism accurately. That’s why referrals and testimonials and critical. Ask their customers if you want to determine whether an MSP is credible, dependable, and trustworthy.

3. Well-Defined Processes

Procedure and process details are a great way to determine the quality of a penetration testing provider. Ensure the company you consider provides proposal details that include:

  • Scope
  • Project methodology
  • Team selection
  • Rules of engagement
  • Risks involved
  • Reporting
  • Handling of PII data management
  • Escalation

Since reporting is of the utmost importance, consider asking for a sample report. You should look for concise, easy-to-understand information and actionable recommendations for discovered vulnerabilities. 

Wrapping Up

The constant threat of a cyberattack looms large, forcing businesses to fortify their cybersecurity strategy. However, proactive penetration testing completed by a reputable provider can help your organization mitigate cybersecurity risk, improve risk posture and keep data breaches at bay.

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