How to Choose a Penetration Test and Evaluate AI Use

Summary

Black Hills Information Security practitioners explain how to choose a penetration test, evaluate AI-assisted testing and establish scope, reporting and remediation expectations.

Key points

• The speakers say AI can accelerate repetitive tasks such as API enumeration and source-code analysis, but human testers remain important for validation, prioritization and mitigation.
• They recommend asking vendors how AI tests are hosted, how customer data is handled, and what controls prevent testing outside the agreed scope.
• Suggested safeguards include logging commands and network traffic, alerting on out-of-scope activity and avoiding persistent model instances across customers.
• Buyers should distinguish vulnerability scanning from penetration testing and select external, internal, assumed-compromise, red-team or purple-team engagements to match their objectives.
• The speakers advise requesting sample reports and clarifying communication, remediation retesting, pricing and rules of engagement before purchasing.
• A speaker described a help-desk social-engineering test in which a single call demonstrated the risk of a password-reset process.

People

Vendors

Tools

Related Articles

• Red Canary’s 2026 Threat Detection Report Highlights Surge in Identity Threat Detectionsgithub.com/jacobdjwilsonAtomic Red Team
• Huntress 2026 Threat Report Finds RMM Abuse Rose 277% in 2025github.com/jacobdjwilsonAtomic Red Team
• Elastic Outlines a Plan-First Method for Cloud Threat Emulationelastic.coAtomic Red Team
• Splunk Threat Research Lead on Threat Hunting, Detection Engineering and Living-Off-the-Land Riskshunt.ioAtomic Red Team