Top 8 Penetration Testing Types, Techniques, and Best Practices

What is Penetration Testing?

Penetration testing, or pentesting, is a simulated cyber-attack against a computer system, network, or application to evaluate its security posture. It involves identifying vulnerabilities, weaknesses, or risks that could be exploited by attackers. The primary goal of penetration testing is to strengthen the target's defenses by understanding how existing security measures respond under real-world attack conditions. This process assists organizations in improving their security by highlighting the areas that need attention.

The pentesting process mimics techniques used by malicious hackers but executed in a controlled environment. Expert penetration testers employ a systematic approach, often using tools and scripts similar to those used in actual cyber attacks. By discovering potential vulnerabilities and assessing their impact, organizations can prioritize remediation efforts, make informed decisions about security policies, and ensure compliance with industry regulations.

Key Types of Penetration Testing

1. Network Penetration Testing

Network penetration testing focuses on identifying and exploiting vulnerabilities within an organization's network infrastructure. This includes routers, switches, firewalls, and other network devices. The goal is to evaluate how network defenses withstand external attacks and identify areas vulnerable to unauthorized access.

Network penetration testing involves:

• Scanning the network for open ports and services using tools like Nmap or Nessus

• Identifying misconfigurations in network devices such as routers, switches, or firewalls

• Attempting to exploit vulnerabilities in protocols like SSH, FTP, or SNMP

• Conducting man-in-the-middle (MITM) attacks to intercept and manipulate network traffic

• Testing network segmentation and lateral movement by simulating internal threats

2. Web Application Penetration Testing

Web application penetration testing involves evaluating the security of web applications, which are often targeted by attackers due to their direct exposure to the internet. Testers scrutinize the application’s design, development, and deployment phases to identify vulnerabilities such as SQL injection, cross-site scripting (XSS), and insecure session management. This form of testing assesses how well web application security measures handle actual attack scenarios.

Web application penetration testing involves:

• Performing injection attacks such as SQL injection and command injection

• Testing for cross-site scripting (XSS) vulnerabilities to exploit user sessions

• Evaluating authentication mechanisms, including password policies and session handling

• Assessing the use of HTTPS and checking for issues like SSL/TLS misconfigurations

• Conducting business logic tests to identify flaws in application workflows

3. Mobile Application Penetration Testing

Mobile application penetration testing evaluates the security of apps on mobile devices, examining areas such as data storage, API interactions, and platform-specific vulnerabilities. Testers assess the application’s resilience to attacks and data leaks by simulating real-world scenarios such as malware injection and data theft.

Mobile penetration testing involves:

• Analyzing local data storage for sensitive information leakage, including insecure storage of credentials

• Testing API interactions for improper authentication or authorization controls

• Assessing mobile-specific vulnerabilities, such as improper platform usage or insufficient cryptography

• Simulating reverse engineering of mobile apps to identify potential code weaknesses

• Testing the app's resilience against malware or malicious apps attempting to exploit it

4. Wireless Network Penetration Testing

Wireless network penetration testing targets the security of wireless communications, aiming to uncover vulnerabilities in Wi-Fi networks. Testers seek to exploit weaknesses in wireless protocols, encryption schemes, and authentication mechanisms. They simulate attacks to understand how well the network protects data in transit and prevents unauthorized access.

Wireless penetration testing involves:

• Identifying weak encryption standards like WEP or misconfigured WPA/WPA2 security

• Conducting attacks such as rogue access points or Evil Twin attacks to intercept wireless traffic

• Testing for vulnerabilities in Wi-Fi Protected Setup (WPS) and exploiting weak passphrases

• Performing denial-of-service (DoS) attacks on the wireless infrastructure to test its resilience

• Assessing the security of wireless client devices against attacks like deauthentication or KRACK

5. Social Engineering Penetration Testing

Social engineering testing simulates attacks that exploit human psychology instead of technical vulnerabilities. Testers attempt to manipulate individuals into divulging confidential information or performing actions that compromise security. This form of testing helps organizations gauge employee awareness and the effectiveness of their training programs.

Social engineering penetration testing involves:

• Phishing campaigns to lure employees into disclosing sensitive information

• Pretexting, where attackers impersonate trusted figures to manipulate victims into revealing data

• Baiting with malicious USB devices or links to entice targets into compromising systems

• Tailgating or piggybacking into restricted areas by exploiting trust in physical security protocols

• Testing the effectiveness of security awareness training through real-world social engineering scenarios

6. Physical Penetration Testing

Physical penetration testing assesses the security of physical premises, aiming to identify vulnerabilities in access controls, alarm systems, and personnel security practices. Testers attempt to bypass physical security barriers, such as locks, surveillance, and security personnel, to gain unauthorized access to facilities or sensitive areas. The objective is to evaluate how effectively an organization’s physical security measures resist intrusion.

Physical penetration testing involves:

• Attempting to bypass physical security measures such as locks, alarms, or badge access systems

• Testing CCTV blind spots or exploiting poorly monitored entry points

• Using covert methods to clone employee access cards or bypass biometric scanners

• Gaining unauthorized access to secure areas by exploiting weaknesses in visitor management systems

• Assessing how well security guards and personnel respond to potential intrusions

7. Cloud Penetration Testing

Cloud penetration testing evaluates security in cloud environments, focusing on configurations, access controls, and data protection in cloud infrastructure. Testers examine vulnerabilities associated with cloud services, virtual machines, and cloud storage, performing tests to identify potential security weaknesses. These tests explore how well cloud setups safeguard data and maintain integrity against compromise.

Cloud penetration testing involves:

• Analyzing cloud service configurations for misconfigured permissions or exposed services

• Testing identity and access management (IAM) policies to identify over-privileged users

• Simulating data exfiltration scenarios to test encryption and access controls on cloud storage

• Testing for vulnerabilities in API endpoints used by cloud services

• Evaluating the security of virtual machines and containers in multi-tenant environments

8. IoT Penetration Testing

IoT penetration testing focuses on devices within the Internet of Things, aiming to assess security vulnerabilities in IoT ecosystems. Testers evaluate device firmware, network communications, and data storage, identifying weaknesses that could be exploited by attackers. This form of testing is critical as IoT devices often lack security, making them prime targets for exploitation.

IoT penetration testing involves:

• Analyzing device firmware for security vulnerabilities and backdoors

• Testing communication protocols for encryption flaws or the use of default credentials

• Assessing the security of IoT cloud integrations and data transfer mechanisms

• Evaluating network segmentation and isolation of IoT devices within broader infrastructure

• Simulating attacks on device ecosystems to explore potential cascading failures in connected devices

Related content: Read our guide to continuous penetration testing

Tips From Our Experts

Mike Belton - Head of Service Delivery

With 25+ years in infosec, Michael excels in security, teaching, and leadership, with roles at Optiv, Rapid7, Pentera, and Madison College.

Use chained exploits for realistic attack simulations

Instead of treating each vulnerability as an isolated incident, chain multiple low-severity vulnerabilities to create high-impact attack vectors. This simulates a more realistic attack scenario and helps assess the true risk of combined weaknesses.

Adopt a threat emulation mindset

Shift from vulnerability identification to adversary emulation by mimicking the tactics, techniques, and procedures (TTPs) of specific threat actors relevant to the organization's industry. This approach provides insights into how well the environment stands up to targeted attacks.

Test default credentials and forgotten systems

Many organizations overlook old, forgotten, or "out-of-scope" systems (e.g., dev environments, unmaintained IoT devices). Always test for default credentials, hardcoded secrets, and legacy systems that could be easy entry points for attackers.

Validate recon against alternate data sources

Use public datasets such as WHOIS, Shodan, and leaked credential databases to enrich your reconnaissance. This can reveal previously unknown entry points like exposed subdomains, open ports, or compromised accounts, extending the attack surface.

Exploit business logic flaws in applications

Beyond technical flaws like SQL injection or XSS, focus on business logic vulnerabilities in web and mobile apps. These include bypassing workflows (e.g., skipping payment steps or gaining unauthorized access to admin functions) which can lead to significant business risks.

Best Practices for Effective Penetration Testing

Most penetration testing programs involve one or more of the testing types above. Here are some best practices that can help make penetration testing more effective, whatever types are being used.

Define Clear Objectives and Scope

Objectives should align with organizational goals and identify what the test aims to achieve, such as identifying specific risks or evaluating security controls. The scope determines the boundaries of the test, addressing which systems, networks, or applications will be tested and any limitations or exclusions.

Clear objectives and scope help guide the testing process, ensuring that efforts focus on areas of highest concern. Detailed planning enables testers to conduct thorough assessments and provide stakeholders with valuable insights into relevant vulnerabilities. Explicit scope definition prevents oversights and resource wastage.

Ensure Legal and Ethical Compliance

Testing activities must adhere to legal requirements and ethical standards, obtaining necessary permissions before commencement. Organizations should follow industry regulations, such as GDPR or HIPAA, and ensure engagements are aligned with the legal frameworks governing their operations.

Ethical compliance involves ensuring consent from stakeholders and transparent communication about testing activities and potential risks. Professional conduct is critical to maintaining trust and integrity throughout the testing process.

Use Qualified and Certified Professionals

Certified testers, such as those with Certified Ethical Hacker (CEH) or Offensive Security Certified Professional (OSCP) credentials, bring expertise and credibility. Their knowledge of current threat landscapes, techniques, and tools ensures thorough and reliable assessments, enhancing test outcomes.

Competent professionals leverage experience to identify and exploit vulnerabilities that non-experts might overlook. Their insights not only highlight immediate security issues but also provide strategic recommendations for long-term risk mitigation.

Regularly Update and Repeat Tests

Cyber threats evolve, making periodic testing essential to identify new vulnerabilities that may arise from system updates, changes, or newly discovered threats. Continuous adaptive testing ensures that security measures remain robust and relevant in face of shifting threat environments.

Routine testing allows organizations to track changes in their security landscape, evaluating the effectiveness of previously implemented measures. This iterative process facilitates constant improvement through timely identification and remediation of vulnerabilities.

Integrate Findings into Security Improvements

Integrating findings from penetration tests into security improvements ensures that identified vulnerabilities are addressed promptly. Pentesting results should inform security policies, enhance existing protections, and guide strategic improvements. Organizations can use these insights to prioritize remediation efforts, closing security gaps and preventing future exploitations.

Effective integration involves communicating findings to stakeholders, translating technical details into actionable recommendations. By aligning results with broader security objectives, organizations can reinforce their defensive strategies.

Adopt Continuous Penetration Testing

Unlike traditional, point-in-time testing, continuous penetration testing involves automated tools that simulate attacks throughout the year, identifying new risks as they emerge. This ongoing approach allows organizations to detect vulnerabilities as soon as changes occur in their systems, such as software updates, infrastructure modifications, or newly exposed attack surfaces.

Continuous penetration testing is particularly useful in dynamic environments where new applications or systems are frequently introduced. It ensures that security teams are always aware of potential weaknesses and can respond rapidly to mitigate risks. By integrating continuous testing into their security framework, organizations can maintain a more resilient defense and reduce the window of exposure to emerging threats.

Learn more about Sprocket Security's Continuous Penetration Testing