A Guide to Manual Penetration Testing

In our previous post on penetration testing, we talked about testing is essential to uncover vulnerabilities that may often go unnoticed. But 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. Automated scans often miss complex vulnerabilities. Manual testing, however, experts simulate realistic attack scenarios and assess your systems with the same creativity and adaptability as potential attackers. 

This approach is especially crucial for industries like 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 Right Pen Test

If you want to use your resources and time efficiently (and prioritize security measures that matter most) choosing the correct type of pen test is essential.

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—you guessed it!—web applications. From forms, login pages, APIs, and other areas where data is exchanged, this type of test simulates attacks that exploit weaknesses in the application’s code, design, and configuration.

Common culprits? Insecure authentication, input validation flaws, and misconfigured API endpoints.

When To Use It

Organizations that handle sensitive data (financial platforms, e-commerce sites, any organization that processes personal or payment information) should prioritize web application pen testing.

It is recommended for apps that are frequently updated or deployed in high-traffic environments where sensitive data is at risk.

Common Use Cases

• Attacks that access unauthorized data by exploiting vulnerabilities in SQL databases.
  
  
• Injecting malicious scripts into web pages viewed by other users.
  
  
• 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

• Identifying open or improperly configured firewall settings that could permit unauthorized access.
  
  
• Detecting outdated software versions that are susceptible to known exploits.
  
  
• 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.

Left unchecked, these could allow unauthorized access to sensitive data or disrupt operations.

When To Use It

This is a good test 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

• Assessing gaps in permissions that could allow unauthorized access to restricted areas or data.
  
  
• Identifying outdated software within the internal network that could be exploited by insiders.
  
  
• Understanding how phishing or social engineering could be leveraged to compromise internal systems.

Network Penetration Testing

Network Penetration Testing zeroes on the security of the organization’s network configurations, data flow, and access controls both 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

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

Segregation and Segmentation Testing

Segregation and segmentation testing evaluates the effectiveness of network segmentation controls. It focuses on the separation between 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

• Verifying that different network segments are properly isolated to restrict access and minimize risk.
  
  
• Testing firewalls to confirm that segmentation rules are effective at preventing unauthorized access.
  
  
• Ensuring that data storage areas are securely partitioned to prevent data leakage across network zones.

API Assessment

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

This 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.

APIs play a critical role in facilitating communication between applications. As such, securing them is crucial for businesses with external-facing APIs or systems that handle sensitive customer data.

Common Use Cases

• Identifying vulnerabilities that could lead to injection attacks (such as SQL injection) which might expose sensitive data.
  
  
• Testing for weaknesses in the API’s authentication mechanisms to prevent unauthorized access.
  
  
• 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 type of testing helps identify gaps in configuration 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

• Checking for misconfigured settings that could unintentionally expose cloud resources to the public.
  
  
• Reviewing access permissions to ensure that only authorized users can access sensitive information.
  
  
• 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

• Testing employees’ reactions to phishing emails to assess awareness levels and uncover potential vulnerabilities.
  
  
• Simulating phone and SMS scams to measure the effectiveness of employee responses to different types of social engineering attacks.
  
  
• 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.

Containers are being used increasingly in enterprise environments, this testing ensures that these environments are properly secured against unauthorized access and vulnerabilities.

Common Use Cases

• Reviewing container images for known vulnerabilities and ensuring secure runtime configurations.
  
  
• Assessing Kubernetes configurations to identify potential misconfigurations that could expose the cluster.
  
  
• Verifying that access controls within the container environment are properly configured to limit permissions based on role.

Red Team Exercises

Red team 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.

They simulate real-world cyberattacks to test security, detection capabilities, and incident response.

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

• Identifying weaknesses in an organization’s detection and response capabilities.
  
  
• Evaluating how quickly and effectively the organization’s security team can respond to an attack.
  
  
• 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. Regular security assessments are required by many regulations. These include:

• PCI DSS for payment data
  
  
• GDPR for data protection
  
  
• HIPAA for healthcare
  
  
• ISO 27001 for information security

These penetration tests cover areas such as internal infrastructure, web applications, cloud security, and employee awareness.

Organizations can demonstrate proactive security practices and strengthen their overall security posture by choosing tests that align with these regulations. 

Tailored Pen Testing and Proactive Monitoring

To address specific vulnerabilities, organizations need a specific type of pen test. 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.

For a continuous security advantage, Codacy complements Bulletproof’s manual testing approach with proactive, automated monitoring through its Software Composition Analysis (SCA) and security dashboard. 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. Together, Codacy and Bulletproof offer a comprehensive, integrated approach to protect your organization’s critical assets and maintain compliance. 

Learn more about Codacy's security solutions or contact out team today to schedule a manual pen testing consultation.