How to Prepare for a Penetration Test

Preparation decides what you get out of the test

How to prepare for a penetration test matters almost as much as the test itself. Running a pentest against the wrong scope, scheduling it during a system migration, or springing it on an unprepared team wastes budget and produces results nobody can act on.

What’s in the checklist

We put together a free, 5-step checklist covering exactly what to do before your engagement starts. Work through it with your team and walk into your next pentest with a scope that’s actually testable and a team that knows what’s coming.

1. Inventory your assets and identify what’s critical

   Servers, cloud tenants, apps, APIs, AI integrations, and which of them would hurt most if an attacker got in.

2. Formalize your scope

   Turn the inventory into a document: IP ranges, domains, app URLs, tenant IDs, and what you are explicitly excluding.

3. Schedule around other IT projects

   Testing during a migration or major deployment turns results into noise. Sequence the pentest after the project lands.

4. Brief your internal team and vendors

   IT, security, your MSSP or MDR, and leadership, before testing begins. Then make a deliberate call on whether the SOC gets advance notice.

5. Lock down rules of engagement

   Points of contact, an emergency stop procedure, the access the test actually needs, and your cloud provider’s testing policies.

Why take this from Red Raine Labs

Red Raine Labs is a Michigan-based, owner-operated penetration testing firm. Every engagement means hands-on exploitation, not automated scanning paired with a template report. We scope engagements the way this checklist describes, because a rushed or vague scope produces a report that doesn’t hold up when you need it, whether that’s for a client, an auditor, or your own leadership.

Already know which test you need?

If you already know you need an External or Internal Network Penetration Test, Web Application Penetration Test, or Cloud Penetration Test, use the checklist first, then bring your scope to a quick call and we’ll finalize it together.