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the basics

Selecting a pentest provider

3/6/2026

5 hard questions every CISO should ask

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last updated on:
3.6.26 15:01

Cutting through the noise: The market is flooded with vendors claiming "Autonomous AI Pentesting." As a CISO, your job is to distinguish a high-end service from an automated data dump.

Use the Woolves "BS-Detector":

  1. "Who is the human in the loop?" If it’s just a junior monitoring a dashboard, it’s not a pentest.
  2. "How do you simulate 'chained' exploits?" Ask for a real-world example where they linked two 'low' findings to gain 'critical' access.
  3. "Is your training data human-validated?" An AI trained on noisy bug bounty data will only produce more noise.
  4. "What is the false-positive rate?" Demand a guarantee that findings are manually verified.
  5. "Does the report include a business impact analysis?" You need to know how a flaw affects your revenue, not just your CVSS score.

The Woolves Verdict: Don't buy a tool. Buy a partnership that understands your business risk.

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