A penetration test is a test by a team of security engineers, using a variety of tools, to test a computer network and identify weaknesses. The broader purpose involves evaluating network vulnerability to actual attacks by simulating real-world hacker techniques.
Key Phases of Penetration Testing
1. Initial Scoping and Agreements
Establishing clear boundaries, timeframes, and contractual terms for what security engineers will test. This ensures both parties understand the scope and limitations of the engagement.
2. Reconnaissance and Scanning
Semi-automated scanning identifies potential vulnerabilities in external or internal environments as defined by the scope. This phase maps out the attack surface and discovers potential entry points.
3. Social Engineering
When included in the scope, this phase uses:
- Phone calls (vishing)
- Emails (phishing)
- Site visits (physical social engineering)
These techniques test employee security awareness and attempt credential acquisition through human manipulation rather than technical exploits.
4. Human Intervention and Gaining Access
Security professionals exploit identified vulnerabilities to access systems. This may include:
- Exploiting unpatched servers
- Leveraging weak passwords
- Using compromised credentials obtained through social engineering
- Chaining multiple vulnerabilities together
5. Collection of Evidence
Teams move laterally through networks to document exploitable weaknesses and gather data samples. This demonstrates the real-world impact of discovered vulnerabilities.
6. Reporting
Documentation of findings with proposed security improvements represents the project's most critical phase. A quality report provides actionable recommendations prioritized by risk level.
Penetration Testing vs. Vulnerability Scanning
Understanding the difference between these two security assessments is crucial:
Penetration Testing
- Involves skilled engineers actively exploiting systems
- Simulates real attacker behavior and techniques
- Tests how vulnerabilities can be chained together
- Provides context about actual business risk
- Requires human expertise and creativity
Vulnerability Scanning
- Uses automated tools to identify known weaknesses
- Produces lists of potential vulnerabilities
- Does not verify if vulnerabilities are exploitable
- Faster and less expensive than penetration testing
- Often incorporated as one component of a penetration test
Getting Started with Penetration Testing
When planning a penetration test, consider the following:
Determine Compliance Requirements
Identify which frameworks or regulations require penetration testing for your organization:
- PCI-DSS (required annually for merchants handling card data)
- NIST 800-53 (federal information systems)
- HIPAA (healthcare organizations)
- SOC 2 (service organizations)
Create an Environment Inventory
Document all environments that need testing:
- External-facing systems and applications
- Internal network infrastructure
- Cloud environments
- Mobile applications
- Web applications
Select the Right Vendor
Choose vendors who provide:
- Customized analysis beyond automated reports
- Experienced security engineers
- Clear methodology and communication
- Actionable recommendations
Human expertise matters significantly in producing actionable security insights.
Key Takeaways
- Penetration testing simulates real-world attacks to identify security weaknesses
- The process includes scoping, reconnaissance, exploitation, and detailed reporting
- Social engineering may be included to test human security awareness
- Penetration testing differs from vulnerability scanning by actively exploiting systems
- Many compliance frameworks require regular penetration testing
- Quality results depend on skilled human security engineers, not just automated tools