What is Penetration Testing?

Penetration testing, commonly known as "pen testing," is a simulated cyber attack against computer systems to check for exploitable vulnerabilities. For Australian businesses, penetration testing provides crucial insights into security weaknesses and helps validate the effectiveness of existing security controls.

How Penetration Testing Works

Penetration testing follows a structured methodology to simulate real-world attacks:

1. Planning and Reconnaissance

Initial phase focusing on information gathering:

• Scope definition: Define testing boundaries and objectives
• Information gathering: Collect publicly available information
• Network mapping: Identify network infrastructure and services
• Target identification: Identify potential attack vectors

2. Scanning and Enumeration

Technical analysis of target systems:

• Port scanning: Identify open ports and services
• Vulnerability scanning: Automated vulnerability identification
• Service enumeration: Detailed analysis of running services
• Operating system fingerprinting: Identify system types and versions

3. Gaining Access

Attempt to exploit identified vulnerabilities:

• Exploit development: Create or adapt exploits for vulnerabilities
• Social engineering: Test human factors in security
• Password attacks: Test password strength and policies
• Application attacks: Test web applications and APIs

4. Maintaining Access

Simulate advanced persistent threat (APT) behavior:

• Persistence mechanisms: Establish ongoing access
• Privilege escalation: Gain higher-level system access
• Lateral movement: Move through network to access additional systems
• Data exfiltration: Test data protection controls

5. Analysis and Reporting

Document findings and provide remediation guidance:

• Vulnerability documentation: Detailed description of findings
• Risk assessment: Evaluate business impact of vulnerabilities
• Remediation recommendations: Specific steps to address issues
• Executive summary: High-level findings for management

Types of Penetration Testing

Network Penetration Testing

Focus: Network infrastructure and perimeter security

Scope includes:

• Firewall configuration and bypass techniques
• Router and switch security
• Network segmentation effectiveness
• Wireless network security
• VPN and remote access security

Web Application Penetration Testing

Focus: Web applications and APIs

Common tests include:

• SQL injection and database attacks
• Cross-site scripting (XSS) vulnerabilities
• Authentication and session management
• Input validation and sanitization
• Business logic flaws

Wireless Penetration Testing

Focus: Wireless network security

Testing areas:

• Wi-Fi encryption and authentication
• Rogue access point detection
• Wireless client security
• Bluetooth and IoT device security

Social Engineering Testing

Focus: Human factors in security

Methods include:

• Phishing email campaigns
• Phone-based social engineering
• Physical security testing
• USB drop attacks

Penetration Testing Methodologies

OWASP Testing Guide

Comprehensive web application security testing framework:

• Information gathering and reconnaissance
• Configuration and deployment management testing
• Identity management and authentication testing
• Authorization and session management testing
• Input validation and error handling testing

NIST SP 800-115

Technical guide to information security testing and assessment:

• Planning phase activities and considerations
• Discovery phase techniques and tools
• Attack phase methodologies
• Reporting phase requirements and best practices

PTES (Penetration Testing Execution Standard)

Comprehensive penetration testing methodology:

• Pre-engagement interactions and scoping
• Intelligence gathering and threat modeling
• Vulnerability analysis and exploitation
• Post-exploitation and reporting

Compliance and Regulatory Requirements

Essential Eight Framework

The Essential Eight framework recommends regular penetration testing:

• Maturity Level 2: Annual penetration testing
• Maturity Level 3: Continuous security testing
• Scope requirements: Test all internet-facing systems
• Remediation timelines: Address findings within specified timeframes

Industry-Specific Requirements

Financial Services

• APRA requirements: Regular security testing for ADIs
• PCI DSS: Annual penetration testing for payment systems
• Scope: All systems handling financial data

Healthcare

• Privacy Act compliance: Test systems handling health records
• Medical device testing: IoMT and connected device security
• Patient safety: Ensure testing doesn't impact care

Government

• ISM requirements: Regular security testing mandates
• Security clearances: Vetted testing personnel
• Classified systems: Specialized testing procedures

Penetration Testing Best Practices

Pre-Testing Preparation

• Clear scope definition: Define testing boundaries and limitations
• Legal agreements: Signed authorization and liability agreements
• Stakeholder notification: Inform relevant teams about testing
• Backup procedures: Ensure systems are backed up before testing

During Testing

• Communication protocols: Regular updates on testing progress
• Emergency procedures: Stop testing if systems are impacted
• Evidence collection: Document all findings with screenshots
• Minimal impact: Avoid disrupting business operations

Post-Testing Activities

• Detailed reporting: Comprehensive findings documentation
• Remediation planning: Prioritized action plan for fixes
• Retest validation: Verify fixes address identified issues
• Lessons learned: Update security policies and procedures

Working with Penetration Testing Providers

Many Australian businesses partner with experienced cybersecurity MSPs for penetration testing services. Leading providers like Affinity MSP offer comprehensive testing services including:

• Network and infrastructure penetration testing
• Web application security assessments
• Social engineering and phishing simulations
• Wireless network security testing
• Compliance-focused testing programs

Selecting a Penetration Testing Provider

Key criteria for choosing testing providers:

• Certifications: OSCP, CEH, GPEN certified testers
• Methodology: Structured testing approach and documentation
• Industry experience: Experience in your sector
• Australian presence: Local operations and compliance knowledge
• Insurance coverage: Professional indemnity and liability coverage

Penetration Testing Frequency

Regular Testing Schedule

Recommended testing frequency by organization type:

• High-risk organizations: Quarterly testing
• Medium-risk organizations: Semi-annual testing
• Low-risk organizations: Annual testing
• After major changes: Test after significant system changes

Continuous Security Testing

Modern approaches to ongoing security validation:

• Automated vulnerability scanning: Continuous vulnerability assessment
• Red team exercises: Ongoing adversarial testing
• Bug bounty programs: Crowdsourced vulnerability discovery
• Purple team activities: Collaborative red and blue team exercises