As a certified penetration tester, conducting comprehensive annual security assessments requires a structured methodology that balances thorough coverage with practical execution. This guide outlines the essential testing procedures, tools, and automation strategies needed to deliver actionable security insights that protect your clients’ critical assets throughout the year.

Infrastructure Pentest

Infrastructure penetration testing forms the foundation of any comprehensive security assessment, targeting the underlying systems, networks, and cloud environments that support business operations. This phase focuses on identifying vulnerabilities in network architecture, system configurations, and cloud security posture that attackers could exploit to gain unauthorized access or escalate privileges.

Cloud Security Assessment

AWS Security Analysis

  • Run Prowler security assessment - Automated AWS security best practices scanner detecting 240+ security checks
  • Review IAM policies and permissions - Identify overprivileged roles like wildcard policies (similar to Capital One breach)
  • Check S3 bucket configurations - Test for public read/write access and encryption settings
  • Analyze VPC and security group settings - Verify network isolation and ingress/egress rules
  • Review CloudTrail logging configuration - Ensure audit logging for compliance and incident response

Multi-Cloud Assessment

  • Execute ScoutSuite across cloud providers - Multi-cloud security posture assessment tool for AWS, Azure, GCP
  • Review Azure security configurations - Check for misconfigurations in Azure AD and resource permissions
  • Assess Google Cloud Platform settings - Verify IAM bindings and compute instance security
  • Check cross-cloud security posture - Identify security gaps across hybrid cloud environments

Microsoft Defender Integration

  • Review Microsoft Defender alerts and policies - Analyze threat detection rules and security baselines
  • Check endpoint protection coverage - Verify EDR deployment and configuration effectiveness
  • Analyze threat intelligence feeds - Review IOC integration and threat hunting capabilities
  • Assess incident response capabilities - Test automated response workflows and escalation procedures

Network Infrastructure Testing

Network Discovery

  • Port scanning with Nmap - Identify open ports and running services using TCP/UDP scanning techniques
  • Service enumeration - Banner grabbing and version detection for attack surface mapping
  • Network topology mapping - Discover network architecture and potential attack paths
  • VLAN and subnet identification - Map network segmentation and trust boundaries

Vulnerability Assessment

  • Run Nessus or OpenVAS scans - Automated vulnerability scanning for CVEs like EternalBlue (MS17-010)
  • Identify unpatched systems - Find systems vulnerable to known exploits like BlueKeep (CVE-2019-0708)
  • Check for default credentials - Test common username/password combinations on network devices
  • Assess network device configurations - Review firewall rules, router configs, and switch security

Network Penetration

  • Attempt lateral movement - Test network traversal using techniques like SMB relay attacks
  • Test network segmentation - Verify isolation between network zones and VLANs
  • Analyze firewall rules - Identify rule bypasses and misconfigurations allowing unauthorized access
  • Check for privilege escalation opportunities - Test for local exploits and weak service permissions

System-Level Testing

Operating System Assessment

  • Check for OS vulnerabilities - Test for kernel exploits like DirtyPipe (CVE-2022-0847) and privilege escalation
  • Review user account configurations - Identify weak passwords, privileged accounts, and dormant users
  • Assess file system permissions - Check for world-writable files and SUID/SGID binaries
  • Test backup and recovery procedures - Verify backup integrity and test restore capabilities

Service Analysis

  • Enumerate running services - Identify unnecessary services and potential attack vectors
  • Test service configurations - Check for insecure service settings and weak authentication
  • Check for service vulnerabilities - Test for service-specific exploits like Apache Struts (CVE-2017-5638)
  • Analyze service account permissions - Review service account privileges and access rights

Web Application Pentest

Web application security testing represents the most dynamic aspect of penetration testing, as applications frequently change and introduce new attack vectors. This comprehensive approach combines automated scanning tools with manual testing techniques to identify vulnerabilities across the OWASP Top 10 and beyond, ensuring thorough coverage of both common and complex security flaws.

Automated Scanning

Burp Suite Professional

  • Configure and run automated scan - Comprehensive web app scanner detecting OWASP Top 10 vulnerabilities
  • Review identified vulnerabilities - Analyze scanner results for SQL injection, XSS, and authentication flaws
  • Perform manual verification of findings - Validate automated findings to eliminate false positives
  • Generate detailed vulnerability reports - Document exploitable vulnerabilities with proof-of-concept

OWASP ZAP Assessment

  • Execute baseline scan - Passive scanning to identify security headers and basic vulnerabilities
  • Run full active scan - Automated testing for injection flaws and security misconfigurations
  • Review spider results - Analyze application structure and identify hidden endpoints
  • Analyze security headers - Check for missing headers like CSP, HSTS, and X-Frame-Options

Manual Testing Categories

Cross-Site Scripting (XSS)

  • Test for reflected XSS - Inject scripts in URL parameters similar to MySpace worm vulnerabilities
  • Check for stored XSS vulnerabilities - Test persistent script injection in user-generated content
  • Assess DOM-based XSS - Client-side script injection through DOM manipulation
  • Verify XSS filtering and encoding - Test bypass techniques against input validation and output encoding

Cross-Site Request Forgery (CSRF)

  • Test CSRF token implementation - Verify anti-CSRF tokens are properly validated and unique
  • Check for state-changing operations - Test unauthorized actions without proper CSRF protection
  • Verify SameSite cookie attributes - Check cookie security settings preventing cross-site requests
  • Assess anti-CSRF mechanisms - Test referer validation and custom header requirements

Authentication & Session Management

  • Test password policies - Check for weak password requirements and brute force protection
  • Check for account lockout mechanisms - Verify protection against credential stuffing attacks
  • Assess session timeout configurations - Test for proper session expiration and idle timeouts
  • Verify secure session handling - Check for session fixation and hijacking vulnerabilities
  • Test multi-factor authentication - Verify MFA implementation and bypass attempts
  • Check for session fixation vulnerabilities - Test if session IDs change after authentication

Authorization & Access Control

  • Test horizontal privilege escalation - Access other users’ data by manipulating user IDs (IDOR)
  • Check vertical privilege escalation - Attempt to access admin functions with user-level accounts
  • Verify role-based access controls - Test proper enforcement of user roles and permissions
  • Assess direct object references - Test for insecure direct object references (IDOR) vulnerabilities

Input Validation

  • SQL injection testing - Test for database injection similar to Sony Pictures breach (2011)
  • Command injection assessment - Test for OS command execution through user input
  • LDAP injection testing - Test for directory service injection vulnerabilities
  • XML/XXE injection checks - Test for XML External Entity attacks and data disclosure
  • File upload security testing - Test for malicious file upload leading to code execution

Business Logic Testing

  • Test workflow bypasses - Attempt to skip payment or approval steps in business processes
  • Check for race conditions - Test concurrent requests to exploit timing vulnerabilities
  • Assess price manipulation - Test for unauthorized price changes in e-commerce applications
  • Verify transaction integrity - Ensure atomicity and consistency of critical business operations

DevSecOps Security Testing

Container Security

  • Scan images for vulnerabilities - Use tools like Trivy to detect CVEs in base images and dependencies
  • Check for hardened base images - Verify use of minimal images like Alpine or distroless containers
  • Review Dockerfile security practices - Check for secrets in layers and proper user configurations
  • Assess runtime configurations - Verify container isolation and resource limitations

Kubernetes Security

  • Review cluster configurations - Check for insecure API server settings and etcd encryption
  • Check RBAC implementations - Verify proper role-based access control and service account permissions
  • Assess network policies - Test pod-to-pod communication restrictions and ingress/egress rules
  • Verify secrets management - Check for proper secret encryption and rotation policies

CI/CD Pipeline Security

  • Review build process security - Check for supply chain attacks and dependency confusion
  • Check for credential exposure - Scan for hardcoded secrets and API keys in repositories
  • Assess deployment configurations - Verify secure deployment practices and environment isolation
  • Verify security gate implementations - Test automated security controls in deployment pipeline

Code Analysis Integration

  • Static application security testing (SAST) - Automated source code analysis for security vulnerabilities
  • Dynamic application security testing (DAST) - Runtime security testing of deployed applications
  • Software composition analysis (SCA) - Third-party dependency vulnerability scanning
  • Infrastructure as Code (IaC) scanning - Security analysis of Terraform, CloudFormation templates

Automation

Modern penetration testing extends far beyond annual assessments, requiring continuous monitoring and automated testing to maintain security posture throughout the year. This automation strategy transforms point-in-time testing into ongoing security validation, ensuring that new vulnerabilities are detected and addressed promptly while reducing the manual effort required for routine security checks.

Continuous Security Monitoring

Scheduled Vulnerability Scans

  • Set up monthly Prowler automated runs - Scheduled AWS security assessment with 240+ security checks
  • Configure weekly ScoutSuite assessments - Multi-cloud security posture monitoring across AWS, Azure, GCP
  • Schedule quarterly Nessus infrastructure scans - Comprehensive network vulnerability assessment
  • Implement daily web application security scans - Automated OWASP Top 10 testing with DAST tools

CI/CD Pipeline Integration

  • Integrate SAST tools into build pipelines - Pre-commit hooks and merge request security scanning
  • Add DAST scanning to deployment workflows - Automated security testing in staging environments
  • Configure container image vulnerability scanning - Block deployment of images with critical CVEs
  • Set up IaC security scanning automation - Terraform and CloudFormation security policy validation

Cloud Security Automation

  • Deploy cloud security posture management (CSPM) - Real-time cloud configuration monitoring and alerting
  • Configure real-time compliance monitoring - Automated SOC2, PCI-DSS, and ISO27001 compliance checks
  • Set up automated remediation workflows - Auto-fix common misconfigurations like open S3 buckets
  • Implement security configuration drift detection - Alert on unauthorized changes to security baselines

Automated Testing Schedule

Monthly Assessments

  • Full infrastructure penetration testing - Automated network scanning and vulnerability exploitation
  • Web application security scanning - Comprehensive OWASP testing across all web properties
  • Cloud configuration reviews - Multi-cloud security posture assessment and compliance validation
  • Container security assessments - Image vulnerability scanning and runtime security analysis

Quarterly Deep Dives

  • Advanced persistent threat (APT) simulation - Automated red team exercises using frameworks like MITRE ATT&CK
  • Red team exercises - Coordinated attack simulation testing detection and response capabilities
  • Business logic testing automation - Automated workflow and transaction integrity testing
  • Social engineering awareness testing - Phishing simulation and security awareness validation

Annual Reviews

  • Comprehensive security architecture assessment - Full-scale penetration testing across all attack surfaces
  • Threat modeling updates - Annual review and update of threat models and attack scenarios
  • Security control effectiveness evaluation - Assessment of security control performance and gaps
  • Risk assessment refresh - Annual risk analysis and security posture evaluation

This structured approach ensures comprehensive security coverage while building sustainable automation practices that protect your clients year-round. The combination of thorough manual testing and intelligent automation creates a robust security program that adapts to evolving threats and maintains continuous vigilance against emerging attack vectors.