ShipSquad

How to Set Up Penetration Testing

advanced12 minSecurity

Establish a penetration testing program to proactively identify and fix security vulnerabilities.

What You'll Learn

This advanced-level guide walks you through how to set up penetration testing step by step. Estimated time: 12 min.

Step 1: Define testing scope

Determine which systems, networks, and applications are in scope and what testing methods are permitted.

Step 2: Choose your approach

Select between automated scanning tools, manual penetration testing, bug bounty programs, or a combination of all three.

Step 3: Select testing providers

Hire reputable penetration testing firms or set up a bug bounty program on HackerOne or Bugcrowd for continuous security testing.

Step 4: Conduct the assessment

Execute testing with clear rules of engagement, communication channels, and emergency procedures for critical findings.

Step 5: Remediate and retest

Prioritize and fix discovered vulnerabilities, then verify fixes with targeted retesting before closing findings.

Frequently Asked Questions

How often should I conduct penetration tests?

Annual comprehensive penetration tests at minimum. Quarterly for high-risk applications. Continuous through bug bounty programs for ongoing coverage.

Bug bounty or traditional pen test?

Start with traditional penetration tests for structured coverage. Add bug bounty programs once you have mature security practices and vulnerability management processes.

What does a penetration test cost?

Basic web app penetration test costs $5K-15K. Comprehensive testing including infrastructure and mobile costs $15K-50K. Bug bounty programs have variable costs based on findings.

Further Reading

Ready to assemble your AI squad?

10 specialized AI agents. One mission. $99/mo + your Claude subscription.

Start Your Mission