A Guide to Manual Penetration Testing

Penetration testing is a security assessment technique in which authorized testers simulate cyberattacks on a system, network, or application to help reveal vulnerabilities that may otherwise go unnoticed.

However, recognizing the need for pen testing is only the first step. In the same way, you’d seek tests for specific health concerns—X-rays, blood tests, eye exams—different areas of your digital environment require particular types of penetration tests as well. 

Manual penetration testing provides this tailored approach by customizing tests to focus on your digital environment’s specific needs and risks. Unlike automated scans, which may miss complex vulnerabilities, manual testing allows skilled experts to simulate realistic attack scenarios and assess your systems with the same creativity and adaptability as potential attackers. 

This approach is especially crucial for industries with stringent compliance requirements—such as finance, healthcare, and e-commerce—where a single missed vulnerability can have severe financial and reputational impacts.

Through this level of detail, manual pen testing goes beyond identifying weaknesses to offer actionable insights, helping strengthen your security posture in the areas that matter most.

Choosing the correct type of pen test is crucial for efficiently using resources, optimizing time, and prioritizing security measures where they matter most.

By matching the proper test to your unique security needs, you can reinforce your defenses and ensure compliance with industry standards, thus building trust with clients, stakeholders, and regulatory bodies.

Web Application Penetration Testing

Web Application Penetration Testing focuses on identifying vulnerabilities in web applications, including entry points such as forms, login pages, APIs, and other areas where data is exchanged.

This test assesses the security of web applications by simulating attacks that exploit weaknesses in the application’s code, design, and configuration. Common issues include insecure authentication, input validation flaws, and misconfigured API endpoints.

When to Use It

Web application pen testing is essential for applications that handle sensitive data, such as financial platforms, e-commerce sites, and any system that processes personal or payment information.

It is particularly recommended for applications frequently updated or deployed in high-traffic environments where sensitive data is at risk.

Common Use Cases

• SQL Injection: Attacks that exploit vulnerabilities in SQL databases to access unauthorized data.
  
  
• Cross-Site Scripting (XSS): Injecting malicious scripts into web pages viewed by other users.
  
  
• Authentication Bypass: Identifying weak points in login mechanisms to gain unauthorized access.

External Infrastructure Penetration Testing

External Infrastructure Penetration Testing focuses on public-facing assets, such as servers, firewalls, and other perimeter defenses, to assess vulnerabilities accessible from outside the organization’s network. This type of test aims to uncover weaknesses that could allow attackers to infiltrate the network, such as unpatched software, misconfigured security settings, and open ports.

When to Use It

External infrastructure pen testing is critical for any organization with internet-facing infrastructure, especially those reliant on online services.

It is particularly valuable for industries where downtime or unauthorized access to public-facing systems, such as finance, healthcare, and retail, could lead to financial loss.

Common Use Cases

• Misconfigured Firewalls: Identifying open or improperly configured firewall settings that could permit unauthorized access.
  
  
• Unpatched Systems: Detecting outdated software versions that are susceptible to known exploits.
  
  
• Weak Passwords: Finding and remediating systems with weak or default passwords that attackers can easily exploit.

Internal Infrastructure Penetration Testing

Internal Infrastructure Penetration Testing evaluates the security of an organization’s internal networks by simulating insider threats, such as a malicious employee or a compromised user account.

This test assesses internal-facing assets, network segmentation, and controls to identify potential vulnerabilities that could allow unauthorized access to sensitive data or disrupt operations.

When to Use It

Internal infrastructure pen testing is recommended for organizations with complex internal networks, valuable intellectual property, or high-risk data, such as finance, healthcare, and manufacturing sectors.

This testing is essential for any business concerned with protecting sensitive information from threats that originate within the organization or through compromised internal access points.

Common Use Cases

• Access Control Weaknesses: Assessing gaps in permissions that could allow unauthorized access to restricted areas or data.
  
  
• Unpatched Systems: Identifying outdated software within the internal network that insiders could exploit.
  
  
• Employee-Targeted Phishing Risks: Understanding how phishing or social engineering could be leveraged to compromise internal systems.

Network Penetration Testing

Network Penetration Testing focuses on the security of the organization’s network configurations, data flow, and access controls within and between networks.

This type of testing evaluates network segmentation, firewall rules, VPN security, and wireless network protections to ensure secure communication and data integrity.

When to Use It

Network pen testing is suitable for organizations that rely on segmented or heavily monitored networks, such as those in regulated industries or businesses with strict security protocols.

It’s especially relevant for organizations dependent on VPNs for remote access, secure Wi-Fi networks, or complex internal network configurations.

Common Use Cases

• Network Segmentation: Ensuring that network segments are correctly isolated to prevent lateral movement by attackers.
  
  
• Secure VPN Testing: Assessing the security of VPN configurations to prevent unauthorized remote access.
  
  
• Firewall Configuration: Testing firewall rules to verify they effectively block unauthorized traffic and control data flow.

Segregation & Segmentation Testing

Segregation and segmentation testing evaluate the effectiveness of network segmentation controls, focusing on separating sensitive networks and less-critical environments.

This type of testing ensures that data flows and access permissions are strictly defined, preventing unauthorized users from accessing restricted areas.

When to Use It

Segmentation testing is ideal for organizations that handle sensitive data and require a strict separation between various network environments. Industries like finance and healthcare, or any business dealing with confidential information, benefit from this level of separation to prevent cross-contamination between data zones.

Common Use Cases

• Network Zoning: Verifying that different network segments are properly isolated to restrict access and minimize risk.
  
  
• Firewall Rules: Testing firewalls to confirm that segmentation rules are effective at preventing unauthorized access.
  
  
• Secure Data Storage Segregation: Ensuring that data storage areas are securely partitioned to avoid data leakage across network zones.

API assessment

API assessment focuses on evaluating the security of application programming interfaces (APIs), ensuring secure data exchange and proper handling of authentication, authorization, and input validation.

This type of testing helps organizations identify vulnerabilities that could expose systems to unauthorized access or data breaches.

When to Use It

API assessments are essential for organizations that rely on APIs to connect systems, provide services, or support customer interactions. As APIs play a critical role in facilitating communication between applications, securing them is crucial for businesses with external-facing APIs or systems that handle sensitive customer data.

Common Use Cases

• Injection Attacks: Identifying vulnerabilities that could allow injection attacks, such as SQL injection, which might expose sensitive data.
  
  
• Improper Authentication: Testing for weaknesses in the API’s authentication mechanisms to prevent unauthorized access.
  
  
• Insecure Data Transfer: Ensuring data exchanged through APIs is encrypted and secure, reducing the risk of interception.

Cloud Configuration Assessment

A cloud configuration assessment evaluates the security configurations of cloud environments, focusing on settings, permissions, and data protection measures within cloud services like AWS, Azure, or Google Cloud.

This testing type helps identify configuration gaps that could expose data to unauthorized access or vulnerabilities.

When to Use It

This assessment is essential for businesses that use cloud services to store and manage critical or sensitive data.

As more organizations shift their infrastructure to the cloud, ensuring that cloud configurations adhere to best practices becomes crucial to maintaining security and data integrity.

Common Use Cases

• Identifying Misconfigurations: Checking for misconfigured settings that could unintentionally expose cloud resources to the public.
  
  
• Access Control Issues: Reviewing access permissions to ensure that only authorized users can access sensitive information.
  
  
• Non-Compliance with Cloud Security Standards: Verifying that the cloud setup aligns with industry standards like CIS Benchmarks or NIST guidelines.

Phishing/Vishing/Smishing Testing

Phishing, vishing, and smishing tests assess an organization’s resilience to social engineering attacks, evaluating employee responses to simulated email (phishing), phone (vishing), and SMS (smishing) attacks.

These tests help gauge employee awareness and identify areas where additional security training may be required.

When to Use It

This type of testing is beneficial for all organizations, especially those handling sensitive customer or employee data.

Given the prevalence of social engineering attacks, regular testing helps organizations prepare their staff to recognize and respond to potential threats.

Common use cases

• Identifying Susceptibility to Phishing: Testing employees’ reactions to phishing emails to assess awareness levels and uncover potential vulnerabilities.
  
  
• Evaluating Vishing and Smishing Awareness: Simulating phone and SMS scams to measure the effectiveness of employee responses to different types of social engineering attacks.
  
  
• Assessing Training Effectiveness: Analyzing results to determine if additional or updated security awareness training is necessary.

Kubernetes/Container Security Testing

Kubernetes and container security testing focuses on the security of containerized environments, assessing configurations within Kubernetes clusters and Docker containers.

It evaluates aspects such as container security settings, orchestrator configurations, and policies that govern access and operations within the container ecosystem.

When to Use It

This test is particularly beneficial for organizations using microservices architectures, where containers and Kubernetes are fundamental to the DevOps workflow. As containers become more widespread in enterprise environments, this testing ensures that these environments are adequately secured against unauthorized access and vulnerabilities.

Common Use Cases

• Container Security Evaluation: Reviewing container images for known vulnerabilities and ensuring secure runtime configurations.
  
  
• Orchestration Vulnerabilities: Assessing Kubernetes configurations to identify potential misconfigurations that could expose the cluster.
  
  
• Role-Based Access Controls: Verifying that access controls within the container environment are correctly configured to limit permissions based on role.

Red Team Exercises

Red team exercises simulate real-world cyberattacks, testing an organization’s security defenses, detection capabilities, and incident response. These exercises involve a team of ethical hackers who use tactics, techniques, and procedures similar to those employed by real attackers, aiming to uncover weaknesses in an organization’s defenses.

When to Use It

This form of testing is best suited for organizations with a mature security posture, typically those looking to validate and strengthen their defenses against sophisticated threats. Red team exercises provide deep insights into how an organization would fare in the face of advanced, targeted attacks.

Common Use Cases

• Detecting Security Gaps: Identifying weaknesses in an organization’s detection and response capabilities.
• Response and Mitigation Testing: Evaluating how quickly and effectively the organization’s security team can respond to an attack.
• Enhancing Security Training: Gaining valuable insights into areas where additional training or resources may be needed for incident response.

Compliance Requirements and Penetration Testing

For many organizations, meeting compliance standards is a driving factor behind targeted penetration testing. Regulations like PCI DSS for payment data, GDPR for data protection, HIPAA for healthcare, and ISO 27001 for information security mandate regular security assessments to safeguard sensitive information.

Tailored penetration tests help organizations address these regulatory expectations, covering areas such as internal infrastructure, web applications, cloud security, and employee awareness.

Organizations demonstrate proactive security practices and strengthen their regulatory posture by selecting specific tests that align with compliance requirements. 

Tailored Pen Testing and Proactive Monitoring

Choosing the right type of penetration testing is essential for organizations to address specific vulnerabilities and maintain robust cybersecurity.

Bulletproof’s CREST-certified experts provide hands-on, customizable testing that aligns with each organization’s unique security and compliance needs, from web applications to complex network infrastructures.

Codacy complements Bulletproof’s manual testing approach with proactive, automated monitoring through its Software Composition Analysis (SCA) and security dashboard for a continuous security advantage.

By combining Bulletproof’s targeted assessments with Codacy’s real-time vulnerability detection, organizations can ensure their security measures remain effective against evolving threats.

To maximize your security investment, consult with Bulletproof and Codacy’s experts to identify the most relevant testing and monitoring solutions for your needs. Codacy and Bulletproof offer a comprehensive, integrated approach to protect your organization’s critical assets and maintain compliance in today’s complex threat landscape. 

Get in touch with us to talk about your penetration testing needs today, or learn more about Codacy's app security features.