diff --git a/README.md b/README.md
index 9ca488a..276a193 100644
--- a/README.md
+++ b/README.md
@@ -25,6 +25,23 @@ Think of it as integration testing for AI tool use.
 
 **Perfect for:** First-time users who want to understand the basics of MCPChecker.
 
+---
+
+### 2. [Evolution Case Study](./evolution-case-study/)
+**Difficulty:** Intermediate
+**Time:** 15-20 minutes
+**What you'll learn:**
+- How documentation quality affects agent success
+- Compare bad vs good tool documentation (2 iterations)
+- See identical code produce different test results
+- Understand what makes tools discoverable when they overlap in functionality
+
+**Perfect for:** Users who want to see MCPChecker's real value and learn documentation best practices.
+
+**Key insight:** Same functionality (4 text processing tools), different documentation = different test results. Proves MCPChecker tests discoverability, not just functionality.
+
+---
+
 ## Getting Help
 
 - 📖 [Full Documentation](https://github.com/mcpchecker/mcpchecker)
diff --git a/evolution-case-study/README.md b/evolution-case-study/README.md
new file mode 100644
index 0000000..c1b6323
--- /dev/null
+++ b/evolution-case-study/README.md
@@ -0,0 +1,270 @@
+# Case Study: Evolving from Bad to Good MCP Tooling
+
+> **See how documentation quality affects AI agent success**
+
+This case study demonstrates the power of MCPChecker by showing the same MCP server with **identical functionality** but **different documentation quality**.
+
+## The Experiment
+
+We have **one text processing server** with 4 tools, all text transformation-related:
+- `process` / `to_uppercase` - Convert to uppercase
+- `transform` / `to_lowercase` - Convert to lowercase
+- `convert` / `to_title_case` - Convert to title case
+- `format_text` / `capitalize_first` - Capitalize first letter only
+
+**The implementation is identical across both iterations. Only the documentation changes.**
+
+## Why Text Processing Tools?
+
+All 4 tools "transform text" but in different ways. With bad documentation (generic names), the agent can't tell which tool does what. With good documentation, it's crystal clear.
+
+## Two Iterations
+
+### Iteration 1: Bad Documentation
+**Location:** `iteration-1-bad/`
+
+Misleading generic names, vague descriptions, no type hints:
+
+```python
+@mcp.tool()
+def process(text: str) -> str:
+    """Process text"""
+    return text.upper()
+
+@mcp.tool()
+def transform(text: str) -> str:
+    """Transform text"""
+    return text.lower()
+
+@mcp.tool()
+def convert(text: str) -> str:
+    """Convert text"""
+    return text.title()
+
+@mcp.tool()
+def format_text(text: str) -> str:
+    """Format text"""
+    return text.capitalize()
+```
+
+**Problems:**
+- ❌ Misleading generic names (`process`, `transform`, `convert`, `format_text`)
+- ❌ Names give ZERO hint about what transformation they perform
+- ❌ Vague descriptions (doesn't explain what processing/transforming means)
+- ❌ No examples
+- ❌ No guidance on **when** to use each tool
+- ❌ "Process text" could mean anything - uppercase? lowercase? something else?
+
+### Iteration 2: Good Documentation
+**Location:** `iteration-2-good/`
+
+Full docstrings with examples, clear names, use case guidance:
+
+```python
+@mcp.tool()
+def to_uppercase(text: str) -> str:
+    """Convert all letters in text to uppercase (capital letters).
+
+    Use this tool when you need text in ALL CAPS format. Every lowercase
+    letter becomes uppercase, while numbers and symbols remain unchanged.
+
+    Args:
+        text: The text to convert to uppercase
+
+    Returns:
+        The text with all letters converted to uppercase
+
+    Example:
+        to_uppercase("hello world") returns "HELLO WORLD"
+        to_uppercase("Hello World 123!") returns "HELLO WORLD 123!"
+    """
+    return text.upper()
+
+@mcp.tool()
+def to_lowercase(text: str) -> str:
+    """Convert all letters in text to lowercase (small letters).
+
+    Use this tool when you need text in all lowercase format. Every uppercase
+    letter becomes lowercase, while numbers and symbols remain unchanged.
+
+    Args:
+        text: The text to convert to lowercase
+
+    Returns:
+        The text with all letters converted to lowercase
+
+    Example:
+        to_lowercase("HELLO WORLD") returns "hello world"
+        to_lowercase("Hello World 123!") returns "hello world 123!"
+    """
+    return text.lower()
+
+# ... and so on for to_title_case and capitalize_first
+```
+
+**Best practices:**
+- ✅ Descriptive names (`to_uppercase`, `to_lowercase`, `to_title_case`)
+- ✅ Full docstrings with Args/Returns
+- ✅ Examples provided
+- ✅ Explains **when** to use each tool
+- ✅ Clarifies the differences between similar tools
+- ✅ "ALL CAPS format" vs "all lowercase format" - immediately clear
+
+## The Test Tasks
+
+Both iterations are tested with the **same natural language prompts** that don't mention tool names.
+
+> **Note:** The examples below are simplified pseudocode to illustrate the test concepts. The actual test files use the full MCPChecker YAML structure. See `evals/tasks/` directories for complete task definitions.
+
+### Task 1: Uppercase Conversion
+```yaml
+prompt: |
+  I have this text: hello world
+
+  Please convert it to all uppercase letters.
+verify: Result contains "HELLO WORLD"
+expected_tool: process (bad) / to_uppercase (good)
+```
+
+### Task 2: Lowercase Conversion
+```yaml
+prompt: |
+  I have this text: HELLO WORLD
+
+  Please convert it to all lowercase letters.
+verify: Result contains "hello world"
+expected_tool: transform (bad) / to_lowercase (good)
+```
+
+### Task 3: Title Case
+```yaml
+prompt: |
+  I have this text: hello world
+
+  Please format it with title case (first letter of each word capitalized).
+verify: Result contains "Hello World"
+expected_tool: convert (bad) / to_title_case (good)
+```
+
+## Actual Results
+
+Since the **code is identical**, differences in test results prove documentation quality matters:
+
+| Task | Iteration 1 (Bad Docs) | Iteration 2 (Good Docs) |
+|------|------------------------|-------------------------|
+| Uppercase conversion | ❌ FAILED (assertions) | ✅ PASSED |
+| Lowercase conversion | ❌ FAILED (assertions) | ✅ PASSED |
+| Title case formatting | ❌ FAILED | ✅ PASSED |
+
+**Actual pass rates:**
+- **Iteration 1 (Bad):** 0/3 tests fully passed, 6/9 assertions passed
+- **Iteration 2 (Good):** 3/3 tests passed, 9/9 assertions passed
+
+> **About assertions:** Each test checks multiple MCP-specific assertions:
+> - **minToolCalls: 1** - Agent must call at least one tool (can't just calculate the answer)
+> - **maxToolCalls: 5** - Agent can't try unlimited tools (prevents brute-force guessing)
+> - **toolsUsed** - Agent must call the specific expected tool (e.g., `to_uppercase` for uppercase conversion)
+>
+> In the bad iteration, the agent sometimes got the correct output but failed because it called the wrong tool or tried too many tools trying to figure out which generic name did what.
+
+**What happened in the bad iteration:**
+- Agent couldn't discover which generic tool (`process`, `transform`, `convert`) does what
+- Even when it got correct answers (by exploring tools), it failed assertions because it didn't call the expected tools
+- Generic names like "process text" don't hint at uppercase conversion
+
+**What happened in the good iteration:**
+- Clear tool names (`to_uppercase`, `to_lowercase`) made it obvious which to use
+- Agent found the correct tools immediately
+- All tests passed
+
+## Running the Case Study
+
+### Prerequisites
+
+See [getting-started](../getting-started/) for installation of:
+- Claude Code
+- mcpchecker
+- uv (Python package manager)
+
+Set judge LLM environment variables:
+```bash
+export JUDGE_BASE_URL="https://api.openai.com/v1"
+export JUDGE_API_KEY="sk-your-key-here"
+export JUDGE_MODEL_NAME="gpt-4o-mini"
+```
+
+### Run Both Iterations
+
+**Iteration 1 - Bad Documentation:**
+```bash
+cd iteration-1-bad
+
+# Terminal 1: Start server
+cd server
+PORT=8000 ./server.py
+
+# Terminal 2: Run tests
+cd evals
+mcpchecker check eval.yaml
+```
+
+**Iteration 2 - Good Documentation:**
+```bash
+cd iteration-2-good
+
+# Terminal 1: Start server (stop previous first)
+cd server
+PORT=8000 ./server.py
+
+# Terminal 2: Run tests
+cd evals
+mcpchecker check eval.yaml
+```
+
+### Compare Results
+
+After running both, compare the JSON output files:
+- `text-processing-bad-test-out.json`
+- `text-processing-good-test-out.json`
+
+You'll see the same code producing different test results based purely on documentation quality.
+
+## Key Takeaways
+
+1. **Similar tools need clear differentiation** - When multiple tools do related things (text transformations), documentation is critical
+2. **MCPChecker validates discoverability** - Tests pass/fail based on whether agents can find and use the RIGHT tool
+3. **Generic names are useless** - `process`, `transform`, `convert` give zero hint about what the tool does, compared to `to_uppercase`, `to_lowercase`, `to_title_case`
+4. **Examples clarify usage** - Iteration 2's examples help agents understand exactly what each transformation does
+5. **"Use this when..." guidance matters** - Explicitly stating use cases prevents tool confusion
+6. **Vague descriptions hurt** - "Process text" could mean anything; "Convert all letters to uppercase" is actionable
+
+## Code Comparison
+
+### Side-by-Side: Uppercase Tool
+
+| Iteration 1 (Bad) | Iteration 2 (Good) |
+|-------------------|-------------------|
+| `def process(text: str):` | `def to_uppercase(text: str) -> str:` |
+| `"""Process text"""` | Full docstring with "Use this when...", Args, Returns, Examples |
+| Name gives no hint what processing means | Name clearly indicates uppercase conversion |
+| No examples | 2 examples showing exact usage |
+| Vague "process" | Specific "ALL CAPS format" description |
+
+The **exact same implementation** (`return text.upper()`) but vastly different discoverability.
+
+## What This Proves
+
+MCPChecker doesn't just test if your tools **work** - it tests if they're **usable by AI agents**.
+
+You can have perfectly functional code that fails MCPChecker tests because:
+- Tool names are misleading or generic (`process`, `transform` tell you nothing)
+- Descriptions don't explain differences between similar tools
+- No examples to learn from
+- Unclear when to use this tool vs alternatives
+- No guidance on what "processing" or "transforming" actually means
+
+**Good documentation = passing tests = agents can actually use your tools.**
+
+## Next Steps
+
+- Check out the [main documentation](https://github.com/mcpchecker/mcpchecker) for advanced features
diff --git a/evolution-case-study/iteration-1-bad/evals/eval.yaml b/evolution-case-study/iteration-1-bad/evals/eval.yaml
new file mode 100644
index 0000000..ccea7b4
--- /dev/null
+++ b/evolution-case-study/iteration-1-bad/evals/eval.yaml
@@ -0,0 +1,44 @@
+kind: Eval
+metadata:
+  name: "text-processing-bad-test"
+
+config:
+  # Use Claude Code as the AI agent
+  agent:
+    type: "builtin.claude-code"
+
+  # MCP server configuration
+  mcpConfigFile: mcp-config.yaml
+
+  # LLM judge configuration
+  llmJudge:
+    env:
+      baseUrlKey: JUDGE_BASE_URL
+      apiKeyKey: JUDGE_API_KEY
+      modelNameKey: JUDGE_MODEL_NAME
+
+  # Test tasks
+  taskSets:
+    - path: tasks/uppercase.yaml
+      assertions:
+        toolsUsed:
+          - server: text-server
+            tool: process
+        minToolCalls: 1
+        maxToolCalls: 5
+
+    - path: tasks/lowercase.yaml
+      assertions:
+        toolsUsed:
+          - server: text-server
+            tool: transform
+        minToolCalls: 1
+        maxToolCalls: 5
+
+    - path: tasks/title-case.yaml
+      assertions:
+        toolsUsed:
+          - server: text-server
+            tool: convert
+        minToolCalls: 1
+        maxToolCalls: 5
diff --git a/evolution-case-study/iteration-1-bad/evals/mcp-config.yaml b/evolution-case-study/iteration-1-bad/evals/mcp-config.yaml
new file mode 100644
index 0000000..a175ad1
--- /dev/null
+++ b/evolution-case-study/iteration-1-bad/evals/mcp-config.yaml
@@ -0,0 +1,5 @@
+mcpServers:
+  text-server:
+    type: http
+    url: http://localhost:8000/mcp
+    enableAllTools: true
diff --git a/evolution-case-study/iteration-1-bad/evals/tasks/lowercase.yaml b/evolution-case-study/iteration-1-bad/evals/tasks/lowercase.yaml
new file mode 100644
index 0000000..11e0424
--- /dev/null
+++ b/evolution-case-study/iteration-1-bad/evals/tasks/lowercase.yaml
@@ -0,0 +1,16 @@
+kind: Task
+apiVersion: mcpchecker/v1alpha2
+metadata:
+  name: "lowercase-test"
+  difficulty: easy
+
+spec:
+  verify:
+    - llmJudge:
+        contains: "hello world"
+
+  prompt:
+    inline: |
+      I have this text: HELLO WORLD
+
+      Please convert it to all lowercase letters.
diff --git a/evolution-case-study/iteration-1-bad/evals/tasks/title-case.yaml b/evolution-case-study/iteration-1-bad/evals/tasks/title-case.yaml
new file mode 100644
index 0000000..fd8ce31
--- /dev/null
+++ b/evolution-case-study/iteration-1-bad/evals/tasks/title-case.yaml
@@ -0,0 +1,16 @@
+kind: Task
+apiVersion: mcpchecker/v1alpha2
+metadata:
+  name: "title-case-test"
+  difficulty: medium
+
+spec:
+  verify:
+    - llmJudge:
+        contains: "Hello World"
+
+  prompt:
+    inline: |
+      I have this text: hello world
+
+      Please format it with title case (first letter of each word capitalized).
diff --git a/evolution-case-study/iteration-1-bad/evals/tasks/uppercase.yaml b/evolution-case-study/iteration-1-bad/evals/tasks/uppercase.yaml
new file mode 100644
index 0000000..640a105
--- /dev/null
+++ b/evolution-case-study/iteration-1-bad/evals/tasks/uppercase.yaml
@@ -0,0 +1,16 @@
+kind: Task
+apiVersion: mcpchecker/v1alpha2
+metadata:
+  name: "uppercase-test"
+  difficulty: easy
+
+spec:
+  verify:
+    - llmJudge:
+        contains: "HELLO WORLD"
+
+  prompt:
+    inline: |
+      I have this text: hello world
+
+      Please convert it to all uppercase letters.
diff --git a/evolution-case-study/iteration-1-bad/server/server.py b/evolution-case-study/iteration-1-bad/server/server.py
new file mode 100755
index 0000000..93b2da9
--- /dev/null
+++ b/evolution-case-study/iteration-1-bad/server/server.py
@@ -0,0 +1,42 @@
+#!/usr/bin/env -S uv run --quiet --script
+# /// script
+# requires-python = ">=3.10"
+# dependencies = [
+#     "mcp>=1.1.0",
+# ]
+# ///
+"""Text processing server - Iteration 1: Bad documentation (misleading names)"""
+
+from mcp.server.fastmcp import FastMCP
+
+# Create an MCP server
+mcp = FastMCP("TextProcessing-Bad")
+
+
+@mcp.tool()
+def process(text: str) -> str:
+    """Process text"""
+    return text.upper()
+
+
+@mcp.tool()
+def transform(text: str) -> str:
+    """Transform text"""
+    return text.lower()
+
+
+@mcp.tool()
+def convert(text: str) -> str:
+    """Convert text"""
+    return text.title()
+
+
+@mcp.tool()
+def format_text(text: str) -> str:
+    """Format text"""
+    return text.capitalize()
+
+
+# Run with streamable HTTP transport
+if __name__ == "__main__":
+    mcp.run(transport="streamable-http")
diff --git a/evolution-case-study/iteration-2-good/evals/eval.yaml b/evolution-case-study/iteration-2-good/evals/eval.yaml
new file mode 100644
index 0000000..1ccce07
--- /dev/null
+++ b/evolution-case-study/iteration-2-good/evals/eval.yaml
@@ -0,0 +1,44 @@
+kind: Eval
+metadata:
+  name: "text-processing-good-test"
+
+config:
+  # Use Claude Code as the AI agent
+  agent:
+    type: "builtin.claude-code"
+
+  # MCP server configuration
+  mcpConfigFile: mcp-config.yaml
+
+  # LLM judge configuration
+  llmJudge:
+    env:
+      baseUrlKey: JUDGE_BASE_URL
+      apiKeyKey: JUDGE_API_KEY
+      modelNameKey: JUDGE_MODEL_NAME
+
+  # Test tasks
+  taskSets:
+    - path: tasks/uppercase.yaml
+      assertions:
+        toolsUsed:
+          - server: text-server
+            tool: to_uppercase
+        minToolCalls: 1
+        maxToolCalls: 5
+
+    - path: tasks/lowercase.yaml
+      assertions:
+        toolsUsed:
+          - server: text-server
+            tool: to_lowercase
+        minToolCalls: 1
+        maxToolCalls: 5
+
+    - path: tasks/title-case.yaml
+      assertions:
+        toolsUsed:
+          - server: text-server
+            tool: to_title_case
+        minToolCalls: 1
+        maxToolCalls: 5
diff --git a/evolution-case-study/iteration-2-good/evals/mcp-config.yaml b/evolution-case-study/iteration-2-good/evals/mcp-config.yaml
new file mode 100644
index 0000000..a175ad1
--- /dev/null
+++ b/evolution-case-study/iteration-2-good/evals/mcp-config.yaml
@@ -0,0 +1,5 @@
+mcpServers:
+  text-server:
+    type: http
+    url: http://localhost:8000/mcp
+    enableAllTools: true
diff --git a/evolution-case-study/iteration-2-good/evals/tasks/lowercase.yaml b/evolution-case-study/iteration-2-good/evals/tasks/lowercase.yaml
new file mode 100644
index 0000000..11e0424
--- /dev/null
+++ b/evolution-case-study/iteration-2-good/evals/tasks/lowercase.yaml
@@ -0,0 +1,16 @@
+kind: Task
+apiVersion: mcpchecker/v1alpha2
+metadata:
+  name: "lowercase-test"
+  difficulty: easy
+
+spec:
+  verify:
+    - llmJudge:
+        contains: "hello world"
+
+  prompt:
+    inline: |
+      I have this text: HELLO WORLD
+
+      Please convert it to all lowercase letters.
diff --git a/evolution-case-study/iteration-2-good/evals/tasks/title-case.yaml b/evolution-case-study/iteration-2-good/evals/tasks/title-case.yaml
new file mode 100644
index 0000000..fd8ce31
--- /dev/null
+++ b/evolution-case-study/iteration-2-good/evals/tasks/title-case.yaml
@@ -0,0 +1,16 @@
+kind: Task
+apiVersion: mcpchecker/v1alpha2
+metadata:
+  name: "title-case-test"
+  difficulty: medium
+
+spec:
+  verify:
+    - llmJudge:
+        contains: "Hello World"
+
+  prompt:
+    inline: |
+      I have this text: hello world
+
+      Please format it with title case (first letter of each word capitalized).
diff --git a/evolution-case-study/iteration-2-good/evals/tasks/uppercase.yaml b/evolution-case-study/iteration-2-good/evals/tasks/uppercase.yaml
new file mode 100644
index 0000000..640a105
--- /dev/null
+++ b/evolution-case-study/iteration-2-good/evals/tasks/uppercase.yaml
@@ -0,0 +1,16 @@
+kind: Task
+apiVersion: mcpchecker/v1alpha2
+metadata:
+  name: "uppercase-test"
+  difficulty: easy
+
+spec:
+  verify:
+    - llmJudge:
+        contains: "HELLO WORLD"
+
+  prompt:
+    inline: |
+      I have this text: hello world
+
+      Please convert it to all uppercase letters.
diff --git a/evolution-case-study/iteration-2-good/server/server.py b/evolution-case-study/iteration-2-good/server/server.py
new file mode 100755
index 0000000..3edd88c
--- /dev/null
+++ b/evolution-case-study/iteration-2-good/server/server.py
@@ -0,0 +1,101 @@
+#!/usr/bin/env -S uv run --quiet --script
+# /// script
+# requires-python = ">=3.10"
+# dependencies = [
+#     "mcp>=1.1.0",
+# ]
+# ///
+"""Text processing server - Iteration 2: Good documentation"""
+
+from mcp.server.fastmcp import FastMCP
+
+# Create an MCP server
+mcp = FastMCP("TextProcessing-Good")
+
+
+@mcp.tool()
+def to_uppercase(text: str) -> str:
+    """Convert all letters in text to uppercase (capital letters).
+
+    Use this tool when you need text in ALL CAPS format. Every lowercase
+    letter becomes uppercase, while numbers and symbols remain unchanged.
+
+    Args:
+        text: The text to convert to uppercase
+
+    Returns:
+        The text with all letters converted to uppercase
+
+    Example:
+        to_uppercase("hello world") returns "HELLO WORLD"
+        to_uppercase("Hello World 123!") returns "HELLO WORLD 123!"
+    """
+    return text.upper()
+
+
+@mcp.tool()
+def to_lowercase(text: str) -> str:
+    """Convert all letters in text to lowercase (small letters).
+
+    Use this tool when you need text in all lowercase format. Every uppercase
+    letter becomes lowercase, while numbers and symbols remain unchanged.
+
+    Args:
+        text: The text to convert to lowercase
+
+    Returns:
+        The text with all letters converted to lowercase
+
+    Example:
+        to_lowercase("HELLO WORLD") returns "hello world"
+        to_lowercase("Hello World 123!") returns "hello world 123!"
+    """
+    return text.lower()
+
+
+@mcp.tool()
+def to_title_case(text: str) -> str:
+    """Convert text to title case (first letter of each word capitalized).
+
+    Use this tool when you need proper title formatting where the first
+    letter of every word is uppercase and remaining letters are lowercase.
+    Also known as "Title Case" or "Proper Case".
+
+    Args:
+        text: The text to convert to title case
+
+    Returns:
+        The text with the first letter of each word capitalized
+
+    Example:
+        to_title_case("hello world") returns "Hello World"
+        to_title_case("HELLO WORLD") returns "Hello World"
+        to_title_case("the quick brown fox") returns "The Quick Brown Fox"
+    """
+    return text.title()
+
+
+@mcp.tool()
+def capitalize_first(text: str) -> str:
+    """Capitalize only the first letter of the text.
+
+    Use this tool when you need sentence-style capitalization where only
+    the very first letter is uppercase and everything else is lowercase.
+    Different from title case which capitalizes every word.
+
+    Args:
+        text: The text to capitalize
+
+    Returns:
+        The text with only the first letter capitalized
+
+    Example:
+        capitalize_first("hello world") returns "Hello world"
+        capitalize_first("HELLO WORLD") returns "Hello world"
+    """
+    return text.capitalize()
+
+
+# Run with streamable HTTP transport
+if __name__ == "__main__":
+    mcp.run(transport="streamable-http")