Lesson 06 Real-World Attack Vectors
Theme:

Homework: Real-World Attack Vectors

Objective: Apply your understanding of real-world attack vectors by conducting a threat analysis of actual AI-powered products. This exercise develops the skill of thinking like an attacker — a critical capability for building secure AI systems.

Task 1: Choose 3 Real-World AI Products

Select 3 real AI-powered products from different categories. You may choose from this list or select your own:

CategoryExample Products
AI SearchPerplexity, Google AI Overviews, Bing Copilot, You.com
Code AssistantsGitHub Copilot, Cursor, Codeium, Amazon CodeWhisperer
Email/ProductivityMicrosoft Copilot (Office), Google Gemini (Workspace), Notion AI
Customer SupportIntercom Fin, Zendesk AI, Ada, Drift
Writing/ContentJasper, Copy.ai, Grammarly AI, Writesonic
Agents/AssistantsChatGPT with plugins, Claude with tools, Custom GPTs
SecurityAI-powered SIEM tools, code scanning tools

For each product, briefly describe:

Task 2: Attack Surface Analysis

For each of your 3 products, create an attack surface map using this format:

Product: [Name]
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

DATA INPUT CHANNELS:
  1. [Channel name] — [description, trust level]
  2. [Channel name] — [description, trust level]
  ...

INJECTION POINTS:
  Direct:
    - [How a user could directly inject]
  Indirect:
    - [How an attacker could inject via data sources]
    - [How an attacker could inject via third-party integrations]

AVAILABLE CAPABILITIES:
  - [Capability 1] → Exploitation potential: [low/medium/high]
  - [Capability 2] → Exploitation potential: [low/medium/high]
  ...

POTENTIAL IMPACTS:
  - Data exfiltration: [what data could be stolen]
  - Misinformation: [what could be manipulated]
  - Unauthorized actions: [what actions could be triggered]
  - Reputation/legal: [what liability could result]

Be specific. Do not write generic descriptions — reference the actual features and integrations of each product.

Task 3: Threat Model for the Most Critical Vector

For each of your 3 products, identify the single most critical attack vector and write a focused threat model (~200 words each). Your threat model should address:

Example format:

Product: Perplexity AI
Most Critical Vector: Web Content Poisoning

THREAT MODEL:
An attacker creates web pages with hidden text (CSS-hidden divs,
zero-size font) containing instructions for AI search engines.
When Perplexity retrieves and summarizes these pages, the hidden
instructions influence the generated summary...

Prerequisites: Basic web development skills, a public website
Affected users: Any user who searches for topics covered by the
poisoned pages (potentially millions)
Impact severity: HIGH — misinformation presented as authoritative
AI-generated summaries, potential for financial fraud (fake product
recommendations), reputational damage to referenced businesses
Detection difficulty: LOW — users rarely compare AI summaries
against source pages; hidden text is invisible in browsers
Existing mitigations: Likely some content sanitization, but no
public documentation of specific anti-injection measures
Recommended defenses: Strip hidden/invisible text from retrieved
pages, cross-reference claims across multiple sources, flag
discrepancies between visible and hidden content...

Task 4: Cross-Product Comparison

After completing your analysis, write a brief comparison (150-200 words) addressing:

Self-Check Criteria

Verify your work against these criteria:

Bonus challenge: For one of your three products, research whether any prompt injection attacks have been publicly disclosed or demonstrated. Include a reference to the disclosure (researcher name, date, description) in your analysis. Check security researcher blogs (e.g., Johann Rehberger's "Embracing Red" blog, Simon Willison's blog) and security conference presentations.