One of the best strategies to proactively find security flaws in your company before attackers do is through penetration testing. However, a lot of businesses approach it with either no clear plan at all or, worse, inadequate preparation.
To help you get the most value (and reduce risk), we created this step-by-step penetration testing checklist covering every phase: preparation, execution, and follow-up.
This guide will make sure you don’t overlook any important steps, whether you’re conducting an internal assessment or collaborating with a provider like Bluefire Redteam.
1. Define the Scope
Start by documenting exactly what will be tested:
- Systems and networks (e.g., production environment, staging, cloud assets)
- Applications (web, mobile, APIs)
- Physical locations (if applicable)
Tip: Clarity here avoids misunderstandings, legal issues, and incomplete coverage.
2. Inventory All Assets
Create a full inventory:
- IP addresses
- Domain names
- Cloud services
- Third-party integrations
- Sensitive data flows
This helps prioritize the most critical targets.
3. Establish Objectives and Success Criteria
Be explicit about:
- What you want to learn
- Compliance requirements (PCI-DSS, SOC 2, ISO 27001)
- Specific risks youâre concerned about
- How success will be measured
4. Select the Testing Methodology
Choose your testing approach:
- Black box: No prior knowledge
- Grey box: Partial access/credentials
- White box: Full access to architecture and code
Each has tradeoffs in depth, realism, and cost.
5. Sign NDAs and Authorization Documents
Penetration testing without written authorization can be illegal.
Ensure:
- NDA is signed
- Rules of Engagement are formalized
- Authorization Letter is documented and countersigned
6. Schedule the Test
Coordinate timelines so stakeholders are aware:
- Avoid critical business windows
- Define testing windows (especially if live systems are in scope)
- Establish communication protocols during the engagement
7. Prepare the Internal Team
Notify relevant teams:
- IT and Security Operations
- Help Desk (in case alarms are triggered)
- Business owners of the systems under test
8. Perform Reconnaissance
Your testers will gather as much information as possible:
- Open ports
- Public records (WHOIS, DNS)
- Employee information (LinkedIn, social media)
Recon lays the groundwork for targeted attacks.
9. Conduct Vulnerability Scanning
Identify known vulnerabilities:
- Unpatched software
- Misconfigurations
- Weak encryption
- Exposed services
10. Exploit Vulnerabilities
Testers attempt real-world attacks:
- Brute-force credentials
- Exploit injection points
- Elevate privileges
- Lateral movement across networks
This phase demonstrates the true risk of each finding.
11. Document All Findings
Throughout the engagement, document:
- Evidence of successful exploits
- Screenshots
- Impact assessments
Clear documentation makes remediation actionable.
12. Contain and Clean Up
Remove any test accounts or artifacts:
- Temporary users or credentials
- Test data
- Residual tools/scripts
13. Deliver the Final Report
A professional report should include:
- Executive summary
- Detailed findings
- Risk ratings
- Recommendations
Tip: Make sure your provider offers a readout meeting to explain results.
14. Remediate Vulnerabilities
Prioritize fixes by risk:
- Critical issues first
- Medium and low risk next
- Validate with evidence of remediation
15. Schedule Retesting
Retesting confirms vulnerabilities are resolved:
- Compare before/after
- Update compliance evidence
- Build trust with stakeholders
Ready to Take the Next Step?
At Bluefire Redteam, we help companies like yours secure their systems with thorough, actionable penetration tests.
- Certified ethical hackers
- Clear, easy-to-understand reports
- Transparent pricing
