Simulated LLM Recon for Pentesters

Mirror probing Copilot queries and surface the sensitive insights they could infer, fueling red-team reports that drive action.

The Scenario

AI tools like Copilot create a new recon layer for pentesters: indirect, inference-based data access. With a single chat, a standard user might uncover salary figures, M&A plans, or patient data. To take action, leadership demands evidence of risks, not just theories.

How It Works: Outcome-Driven Steps

Create a Sandbox User

Knostic clones a real non-admin role (intern, contractor) so findings are grounded in actual user access.

Launch Recon Prompts

A library of attacker-style questions probes HR, finance, legal, and IP topics through Copilot.

Trace Inferences

The platform links every answer back to its source, exposing how “harmless” fragments create leaks.

Prioritize Findings

Sort between regulatory sensitivity, affected business units, and potential operational exposure.

Provide Fix Path

Increase security by adjusting labels or ACLs with one click. Then test to make sure you stopped the leaks.

Key Benefits for Red & Blue Teams

Concrete Evidence of Risk

Show executives the exact prompts and leaked insights, not just IP addresses and hashes.

Inference Visibility

Captures data assembled from multiple files, which legacy DLP misses.

Take Action Faster

Use evidence-based insights to justify deeper red team campaigns or simulate attacker behaviors at scale.

Zero Impact on Prod

Agentless testing means no noise or user disruption.

Ready in Hours

No agents, scripts, or custom code.

How This Use Case Leverages Knostic’s Core Capabilities

Together, these capabilities let pentesters expose real AI-driven gaps, and give defenders an instant roadmap to close them.

No-Code Deployment

Connects to M365 and Copilot in minutes, enabling rapid red-team cycles.

Knowledge Oversharing Detection

Fires natural-language recon prompts and surfaces the sensitive insights Copilot reveals.

Audit Trail of Knowledge Access

Generates a tamper-proof log of prompts, answers, and sources, perfect for post-engagement reports.

Security Control Feedback Loop

Flags DLP/RBAC failures, pushes fixes, and retests to prove remediation.

Remediation Playbooks

Turns each leak into an owner-assigned action plan.

Ready to put your Gen AI assistant through a true red-team? Get your first findings and remediation plan within 24 hours.