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    Penetration testing is often misunderstood or confused with vulnerability assessment. In this article we will review the definition, benefits, and the different types of penetration testing services available to help you make informed decisions about what kind of penetration testing services to engage when you implement a pen testing program.

    What is Penetration Testing?

    Penetration testing, also called pen testing, is a cyber security exercise in which a security testing expert, called a pen tester, identifies and verifies real-world security flaws—vulnerabilities—by simulating the actions of a skilled cybercriminal determined to gain unauthorized access to an organization’s data, systems, and infrastructure.

    What is a Vulnerability Assessment?

    A vulnerability assessment is a systematic review of security weaknesses in an information system. It evaluates whether the system is susceptible to any known vulnerabilities, assigns severity levels to those vulnerabilities, and recommends remediation or mitigation. Vulnerability assessments are most commonly performed using automated vulnerability scanners.

    The absence of a human attacker to leverage those vulnerabilities for exploitation, by themselves or in combination with other vulnerabilities or misconfigurations, is the key distinguishing feature that makes a penetration test a more reliable indicator of the application’s overall risk to exploitation.

    What are the Benefits of Penetration Testing?

    Penetration testing uncovers an organization’s security weaknesses. A pen test rates and prioritizes vulnerabilities by exploitability and risk based on likelihood and impact. This means that if a vulnerability cannot be exploited, then it’s not a vulnerability.

    1. Deliver secure software for less. Despite best efforts, some vulnerabilities slip past the application security checks during development. Secure code review identifies code that might be exploitable and the vulnerabilities identified by a penetration test are proven to be exploitable. 

    2. Avoid breaches. Discover vulnerabilities and exposures early, so you can remediate them and prevent an attack.

    3. Use human insight like attackers do. Threat actors are flexible and creative. Understanding the implications of a vulnerability to a specific application or organization requires human insight.

    4. Achieve compliance. Penetration testing is required to demonstrate cyber security and achieve compliance with regulations and industry standards such as Payment Card Industry Data Security Standard (PCI DSS) and Health Insurance Portability and Accountability Act (HIPAA).

    5. Eliminate false positives. Don’t waste time fixing what is not broken! Focus on exploitability.

    6. Prioritize remediation.  Prioritize remediation by exploitability and actual risk.

    7. Demonstrate business impact. A penetration test will show the real business impact of a vulnerability.

    8. Validate security controls. Ultimately, penetration testing will validate the return on investment of security controls.

    What are the Different Types of Penetration Testing?

    The targets of penetration testing include networks, software applications, the cloud, detective controls, and employee behaviors. Each type of penetration test focuses on a different target.

    Network Penetration Testing

    Network penetration testing, also called network security testing, focuses on internal and external networks, wireless endpoints and wireless networks, email phishing, and other types of social engineering. Five types of network penetration testing are:

    1. External Penetration Testing—Your internet-facing assets are always exposed; sensitive data, clouds, and IoT devices are at the highest risk of attack. Our external penetration testing service identifies security gaps and provides you with actionable guidance to improve security.

    2. Internal Penetration Testing—Vulnerabilities can be anywhere on your network. Our internal network penetration testing service identifies security gaps and provides actionable guidance on how to improve your network security, or help you meet compliance requirements, such as PCI DSS and HIPAA penetration testing.

    3. Wireless Penetration Testing—Wireless devices may put your network at risk. Winmill penetration testing service will identify security issues and provide actionable recommendations for improving your wireless security. Our testing includes wardriving, handshake brute forcing, evil twin attacks, rogue access point detection, and deauthentication attacks.

    Application Penetration Testing

    Application penetration testing focuses on web applications, finding vulnerabilities such as those described in the Open Web Application Security Project® (OWASP) Top Ten and the Common Weakness Enumeration (CWE) Top 25. Types of application penetration testing are:

     1. Web Application Penetration Testing—Winmill pen tests your web applications wherever they are hosted. We employ manual and automated penetration testing processes using commercial, open source, and proprietary security testing tools to evaluate your web application from the perspective of anonymous and authenticated users.

    2. Mobile Application Penetration Testing—Mobile applications can put internal systems, processes, and data at risk. Winmill mobile application security assessments include static and dynamic testing of your Android or iOS applications.

    3. Thick Client Application Penetration Testing—Testing thick client applications for security vulnerabilities requires expert manual penetration testing skills and a thoughtful, methodical approach. (“Thick clients,” sometimes called “fat clients,” are networked computer systems where most of the data and operations reside in local PCs.) Winmill thick client app penetration testing service uses multi-vector cyber security testing to identify design and configuration weaknesses.

    IoT and Embedded Penetration Testing

    IoT (Internet of Things) and embedded device penetration testing focuses on finding critical vulnerabilities that could put your devices and networks at risk of a cyber attack. Penetration testing has become critical for companies that want to understand, assess, and improve the overall security and accountability of their IoT devices and systems.

    Cloud Penetration Testing

    Cloud pen testing focuses on cloud infrastructure. A cloud platform can create exposure from network, application, and configuration vulnerabilities that can result in external access to company credentials, internal systems, and sensitive data.

     AWS & Azure Penetration Testing—Our AWS and Azure penetration testing service identifies cloud configuration and other security issues on your AWS or Azure infrastructure and provides actionable recommendations to improve your AWS or Azure cloud security posture.

    Adversary Simulation and Red Teaming

    Adversary simulation and red team operations are security exercises that assess a company’s ability to identify and respond to real-world attack and breach scenarios in real time. Breach and attack simulation exercises measure the effectiveness of your detective controls to ensure they are identifying attack attempts. Four types of adversary simulation are:

    1. Breach and Attack Simulation—Test your controls against tactics outlined in the MITRE ATT&CK (Adversarial Tactics, Techniques and Common Knowledge) framework or dial into the common techniques used in ransomware attacks.

    2. Red Team Security Operations—Winmill red team operations put your organization’s security controls, security policies, incident response, and cyber security training to the test.

    3. Ransomware Attack Simulation—Are you prepared for a ransomware attack? Ransomware is a top concern for security leaders as the threat grows and incidents become more common. Raise ransomware security awareness in your organization and assess your preventive and detective ransomware security controls against the tactics, techniques, and procedures (TTPs) used by real-world ransomware attackers.

    4. Social Engineering Penetration Testing—Attackers attempt to trick employees into exposing sensitive information every day. Make sure your employees are ready. Winmill social engineering testing helps validate and improve your procedural security controls and employee training.

    In this article we reviewed the definition, benefits, and the different types of penetration testing services that are commonly available to organizations.  Don’t become the next victim of a breach or ransomware attack. Schedule your penetration test today!


    Open Web Application Security Project and Common Weakness Enumeration are trademarks or registered trademarks of their respective owners.