shadow-ai-discovery

Scans your GitHub repositories, Slack workspace, and SSO logs to detect unauthorized AI tool usage. Classifies each finding by risk level and data exposure, then generates a prioritized remediation pl

SKILL.md

GitHub

Shadow AI Discovery

Identify unapproved AI tools being used across your organization and create a remediation plan.

Integrations: Slack, GitHub

When to Use

  • The user wants to find unapproved AI tools being used in their organization
  • Security teams need to audit for "shadow AI" usage
  • The user mentions "shadow AI", "unapproved tools", "AI audit", or "unauthorized AI usage"
  • Compliance requires an inventory of all AI tools in use

Steps

Step 1: Define the Approved Tool List

Ask the user for their list of approved AI tools. If they don't have one, help them create a baseline:

Category Common Approved Tools
Code Generation GitHub Copilot, Cursor, Cline
Chat Assistants ChatGPT Team/Enterprise, Claude, Gemini
Code Review CodeRabbit, Sourcery
Documentation Mintlify, Readme.com
Testing Testim, Mabl

Step 2: Scan for Shadow AI Indicators

Guide the user through these detection methods:

GitHub/GitLab Repository Scan:

  • Search for AI tool configuration files: .cursorrules, .github/copilot, .cline/, .claude/, .openai/, .cursor/
  • Search for AI-related dependencies in package.json, requirements.txt, Gemfile
  • Search for AI API keys in code (patterns: sk-, OPENAI_API_KEY, ANTHROPIC_API_KEY, HUGGINGFACE_TOKEN)
  • Review .gitignore for AI tool patterns being hidden

Slack Workspace Scan:

  • Search for AI tool bot integrations (ChatGPT, Claude, custom bots)
  • Search message history for AI tool mentions and sharing of AI-generated content
  • Review installed Slack apps for AI-related integrations
  • Check for webhook URLs pointing to AI services

Network/SSO Indicators:

  • Review SSO logs for OAuth connections to AI services
  • Check browser extension inventories for AI tools
  • Review DNS logs for AI service domains (api.openai.com, api.anthropic.com, etc.)

Step 3: Classify Discovered Tools

For each discovered tool, classify:

Field Options
Risk Level Low, Medium, High, Critical
Data Exposure None, Internal Only, Confidential, PII/PHI
User Count Estimated number of users
Business Value Low, Medium, High
Compliance Impact None, Minor, Major, Blocking

Step 4: Generate Remediation Plan

For each unapproved tool, recommend one of:

  1. Approve — Tool is low-risk, add to approved list with usage guidelines
  2. Replace — Redirect users to an approved alternative with similar capabilities
  3. Restrict — Allow with conditions (e.g., specific teams only, no sensitive data)
  4. Block — High-risk tool, block access and notify users with alternatives

Step 5: Create Reports

Generate:

  • Executive Summary — Total shadow AI tools found, risk distribution, top recommendations
  • Detailed Inventory — Spreadsheet of all discovered tools with classification
  • Remediation Tracker — Jira tickets or task list with owners and deadlines
  • Communication Template — Message to affected users about policy and approved alternatives

Output

Deliver:

  • Shadow AI inventory spreadsheet
  • Risk-classified remediation plan
  • Communication templates for affected users
  • Updated approved tools list recommendation