Why this checklist exists
Penetration testing can surface dozens—or hundreds—of findings. But the real value comes from a focused test with context, preparation, and clear success criteria. Use this checklist to make sure your team gets the most actionable results possible.
✅ One-Page Preparation Checklist
- Define your objective: What do you want to learn? Prove? Validate?
- Identify in-scope systems: IPs, URLs, cloud accounts, and app versions.
- Share constraints early: Maintenance windows, blacklisted IPs, MFA rules.
- Provide contact points: One technical and one management contact.
- Clarify credentials: Pre-staged accounts, VPNs, or test tenants ready to go.
- Establish success metrics: What does “done” look like?
- Align communication cadence: Daily sync, weekly check-in, or post-test only?
- Prepare your defenders: Will this test be overt or stealth?
- Review reporting expectations: Executive summary vs. technical depth.
- Plan remediation time: Testing is step one; fixing is where value is realized.
💡 Pro tip: Treat your first test as a baseline. The goal isn’t perfection—it's to
build repeatable cycles that tighten security over time.
Common pitfalls to avoid
- Starting without a clear goal (“just test everything”).
- Not involving operations or IT until the last minute.
- Assuming testers can guess your environment’s priorities.
- Skipping post-test debriefs and lessons learned.
Penetration tests are only as valuable as the actions they drive. Invest in the prep, define your outcomes, and you’ll turn a compliance checkbox into a capability multiplier.
Written by:
Chris Coppock — Founder, Red Raven Solutions