diff --git a/docs/README.md b/docs/README.md
index 0b40434..4cac177 100644
--- a/docs/README.md
+++ b/docs/README.md
@@ -16,6 +16,7 @@ This documentation is organized into four main categories to serve different aud
 - **[Development Workflows](contributing/workflows.md)** - Git workflows, testing, and collaboration patterns
 - **[Code Style Guide](contributing/code-style.md)** - Coding standards and best practices
 - **[Testing Strategy](contributing/testing.md)** - Testing approaches and quality assurance
+- **[Test Structure Analysis](contributing/test-structure.md)** - Detailed analysis of existing test suite
 - **[Repository Overview](contributing/file-overview.md)** - Understanding the codebase structure
 
 ### 🏗️ For System Architects
diff --git a/docs/contributing/test-structure.md b/docs/contributing/test-structure.md
new file mode 100644
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+++ b/docs/contributing/test-structure.md
@@ -0,0 +1,470 @@
+# Test Structure Documentation
+
+## Overview
+
+This document provides a comprehensive analysis of the existing test structure in the Gemini MCP Server project. The test suite consists of **17 specialized test files** organized to validate all aspects of the system from unit-level functionality to complex AI collaboration workflows.
+
+## Test Organization
+
+### Test Directory Structure
+
+```
+tests/
+├── __init__.py                     # Package initialization
+├── conftest.py                     # Global test configuration and fixtures
+├── test_claude_continuation.py     # Claude continuation opportunities
+├── test_collaboration.py          # AI-to-AI collaboration features
+├── test_config.py                  # Configuration validation
+├── test_conversation_history_bug.py # Bug fix regression tests
+├── test_conversation_memory.py     # Redis-based conversation persistence
+├── test_cross_tool_continuation.py # Cross-tool conversation threading
+├── test_docker_path_integration.py # Docker environment path translation
+├── test_large_prompt_handling.py  # Large prompt detection and handling
+├── test_live_integration.py       # Live API testing (excluded from CI)
+├── test_precommit.py              # Pre-commit validation and git integration
+├── test_prompt_regression.py      # Normal prompt handling regression
+├── test_server.py                 # Main server functionality
+├── test_thinking_modes.py         # Thinking mode functionality
+├── test_tools.py                  # Individual tool implementations
+└── test_utils.py                  # Utility function testing
+```
+
+## Test Categories and Analysis
+
+### 1. Core Functionality Tests
+
+#### `test_server.py` - Main Server Functionality
+**Purpose**: Tests the core MCP server implementation and tool dispatch mechanism
+
+**Key Test Classes**:
+- **Server startup and initialization**
+- **Tool registration and availability**
+- **Request routing and handling**
+- **Error propagation and handling**
+
+**Example Coverage**:
+```python
+# Tests tool listing functionality
+def test_list_tools()
+
+# Tests tool execution pipeline
+async def test_call_tool()
+
+# Tests error handling for invalid tools
+async def test_call_invalid_tool()
+```
+
+#### `test_config.py` - Configuration Management
+**Purpose**: Validates configuration loading, environment variable handling, and settings validation
+
+**Key Areas**:
+- **Environment variable parsing**
+- **Default value handling**
+- **Configuration validation**
+- **Error handling for missing required config**
+
+#### `test_tools.py` - Tool Implementation Testing
+**Purpose**: Tests individual tool implementations with comprehensive input validation
+
+**Key Features**:
+- **Absolute path enforcement across all tools**
+- **Parameter validation for each tool**
+- **Error handling for malformed inputs**
+- **Tool-specific behavior validation**
+
+**Critical Security Testing**:
+```python
+# Tests that all tools enforce absolute paths
+async def test_tool_absolute_path_requirement()
+
+# Tests path traversal attack prevention
+async def test_tool_path_traversal_prevention()
+```
+
+#### `test_utils.py` - Utility Function Testing
+**Purpose**: Tests file utilities, token counting, and directory handling functions
+
+**Coverage Areas**:
+- **File reading and processing**
+- **Token counting and limits**
+- **Directory traversal and expansion**
+- **Path validation and security**
+
+### 2. Advanced Feature Tests
+
+#### `test_collaboration.py` - AI-to-AI Collaboration
+**Purpose**: Tests dynamic context requests and collaborative AI workflows
+
+**Key Scenarios**:
+- **Clarification request parsing**
+- **Dynamic context expansion**
+- **AI-to-AI communication protocols**
+- **Collaboration workflow validation**
+
+**Example Test**:
+```python
+async def test_clarification_request_parsing():
+    """Test parsing of AI clarification requests for additional context."""
+    # Validates that Gemini can request additional files/context
+    # and Claude can respond appropriately
+```
+
+#### `test_cross_tool_continuation.py` - Cross-Tool Threading
+**Purpose**: Tests conversation continuity across different tools
+
+**Critical Features**:
+- **Continuation ID persistence**
+- **Context preservation between tools**
+- **Thread management across tool switches**
+- **File context sharing between AI agents**
+
+#### `test_conversation_memory.py` - Memory Persistence
+**Purpose**: Tests Redis-based conversation storage and retrieval
+
+**Test Coverage**:
+- **Conversation storage and retrieval**
+- **Thread context management**
+- **TTL (time-to-live) handling**
+- **Memory cleanup and optimization**
+
+#### `test_thinking_modes.py` - Cognitive Load Management
+**Purpose**: Tests thinking mode functionality across all tools
+
+**Validation Areas**:
+- **Token budget enforcement**
+- **Mode selection and application**
+- **Performance characteristics**
+- **Quality vs. cost trade-offs**
+
+### 3. Specialized Testing
+
+#### `test_large_prompt_handling.py` - Scale Testing
+**Purpose**: Tests handling of prompts exceeding MCP token limits
+
+**Key Scenarios**:
+- **Large prompt detection (>50,000 characters)**
+- **Automatic file-based prompt handling**
+- **MCP token limit workarounds**
+- **Response capacity preservation**
+
+**Critical Flow Testing**:
+```python
+async def test_large_prompt_file_handling():
+    """Test that large prompts are automatically handled via file mechanism."""
+    # Validates the workaround for MCP's 25K token limit
+```
+
+#### `test_docker_path_integration.py` - Environment Testing
+**Purpose**: Tests Docker environment path translation and workspace mounting
+
+**Coverage**:
+- **Host-to-container path mapping**
+- **Workspace directory access**
+- **Cross-platform path handling**
+- **Security boundary enforcement**
+
+#### `test_precommit.py` - Quality Gate Testing
+**Purpose**: Tests pre-commit validation and git integration
+
+**Validation Areas**:
+- **Git repository discovery**
+- **Change detection and analysis**
+- **Multi-repository support**
+- **Security scanning of changes**
+
+### 4. Regression and Bug Fix Tests
+
+#### `test_conversation_history_bug.py` - Bug Fix Validation
+**Purpose**: Regression test for conversation history duplication bug
+
+**Specific Coverage**:
+- **Conversation deduplication**
+- **History consistency**
+- **Memory leak prevention**
+- **Thread integrity**
+
+#### `test_prompt_regression.py` - Normal Operation Validation
+**Purpose**: Ensures normal prompt handling continues to work correctly
+
+**Test Focus**:
+- **Standard prompt processing**
+- **Backward compatibility**
+- **Feature regression prevention**
+- **Performance baseline maintenance**
+
+#### `test_claude_continuation.py` - Session Management
+**Purpose**: Tests Claude continuation opportunities and session management
+
+**Key Areas**:
+- **Session state management**
+- **Continuation opportunity detection**
+- **Context preservation**
+- **Session cleanup and termination**
+
+### 5. Live Integration Testing
+
+#### `test_live_integration.py` - Real API Testing
+**Purpose**: Tests actual Gemini API integration (excluded from regular CI)
+
+**Requirements**:
+- Valid `GEMINI_API_KEY` environment variable
+- Network connectivity to Google AI services
+- Redis server for conversation memory testing
+
+**Test Categories**:
+- **Basic API request/response validation**
+- **Tool execution with real Gemini responses**
+- **Conversation threading with actual AI**
+- **Error handling with real API responses**
+
+**Exclusion from CI**:
+```python
+@pytest.mark.skipif(not os.getenv("GEMINI_API_KEY"), reason="API key required")
+class TestLiveIntegration:
+    """Tests requiring actual Gemini API access."""
+```
+
+## Test Configuration Analysis
+
+### `conftest.py` - Global Test Setup
+
+**Key Fixtures and Configuration**:
+
+#### Environment Isolation
+```python
+# Ensures tests run in isolated sandbox environment
+os.environ["MCP_PROJECT_ROOT"] = str(temp_dir)
+```
+
+#### Dummy API Keys
+```python
+# Provides safe dummy keys for testing without real credentials
+os.environ["GEMINI_API_KEY"] = "dummy-key-for-testing"
+```
+
+#### Cross-Platform Compatibility
+```python
+# Handles Windows async event loop configuration
+if platform.system() == "Windows":
+    asyncio.set_event_loop_policy(asyncio.WindowsProactorEventLoopPolicy())
+```
+
+#### Project Path Fixtures
+```python
+@pytest.fixture
+def project_path():
+    """Provides safe project path for file operations in tests."""
+```
+
+### `pytest.ini` - Test Runner Configuration
+
+**Key Settings**:
+```ini
+[pytest]
+testpaths = tests
+python_files = test_*.py
+python_classes = Test*
+python_functions = test_*
+asyncio_mode = auto
+addopts = 
+    -v
+    --strict-markers
+    --tb=short
+```
+
+## Mocking Strategies
+
+### 1. Gemini API Mocking
+
+**Pattern Used**:
+```python
+@patch("tools.base.BaseTool.create_model")
+async def test_tool_execution(self, mock_create_model):
+    mock_model = Mock()
+    mock_model.generate_content.return_value = Mock(
+        candidates=[Mock(content=Mock(parts=[Mock(text="Mocked response")]))]
+    )
+    mock_create_model.return_value = mock_model
+```
+
+**Benefits**:
+- **No API key required** for unit and integration tests
+- **Predictable responses** for consistent testing
+- **Fast execution** without network dependencies
+- **Cost-effective** testing without API charges
+
+### 2. Redis Memory Mocking
+
+**Pattern Used**:
+```python
+@patch("utils.conversation_memory.get_redis_client")
+def test_conversation_flow(self, mock_redis):
+    mock_client = Mock()
+    mock_redis.return_value = mock_client
+    # Test conversation persistence logic
+```
+
+**Advantages**:
+- **No Redis server required** for testing
+- **Controlled state** for predictable test scenarios
+- **Error simulation** for resilience testing
+
+### 3. File System Mocking
+
+**Pattern Used**:
+```python
+@patch("builtins.open", mock_open(read_data="test file content"))
+@patch("os.path.exists", return_value=True)
+def test_file_operations():
+    # Test file reading without actual files
+```
+
+**Security Benefits**:
+- **No file system access** during testing
+- **Path validation testing** without security risks
+- **Consistent test data** across environments
+
+## Security Testing Focus
+
+### Path Validation Testing
+
+**Critical Security Tests**:
+1. **Absolute path enforcement** - All tools must reject relative paths
+2. **Directory traversal prevention** - Block `../` and similar patterns
+3. **Symlink attack prevention** - Detect and block symbolic link attacks
+4. **Sandbox boundary enforcement** - Restrict access to allowed directories
+
+**Example Security Test**:
+```python
+async def test_path_traversal_attack_prevention():
+    """Test that directory traversal attacks are blocked."""
+    dangerous_paths = [
+        "../../../etc/passwd",
+        "/etc/shadow",
+        "~/../../root/.ssh/id_rsa"
+    ]
+    
+    for path in dangerous_paths:
+        with pytest.raises(SecurityError):
+            await tool.execute({"files": [path]})
+```
+
+### Docker Security Testing
+
+**Container Security Validation**:
+- **Workspace mounting** - Verify read-only access enforcement
+- **Path translation** - Test host-to-container path mapping
+- **Privilege boundaries** - Ensure container cannot escape sandbox
+
+## Test Execution Patterns
+
+### Parallel Test Execution
+
+**Strategy**: Tests are designed for parallel execution with proper isolation
+
+**Benefits**:
+- **Faster test suite** execution
+- **Resource efficiency** for CI/CD
+- **Scalable testing** for large codebases
+
+### Conditional Test Execution
+
+**Live Test Skipping**:
+```python
+@pytest.mark.skipif(not os.getenv("GEMINI_API_KEY"), reason="API key required")
+```
+
+**Platform-Specific Tests**:
+```python
+@pytest.mark.skipif(platform.system() == "Windows", reason="Unix-specific test")
+```
+
+## Test Quality Metrics
+
+### Coverage Analysis
+
+**Current Test Coverage by Category**:
+- ✅ **Tool Functionality**: All 7 tools comprehensively tested
+- ✅ **Server Operations**: Complete request/response cycle coverage
+- ✅ **Security Validation**: Path safety and access control testing
+- ✅ **Collaboration Features**: AI-to-AI communication patterns
+- ✅ **Memory Management**: Conversation persistence and threading
+- ✅ **Error Handling**: Graceful degradation and error recovery
+
+### Test Reliability
+
+**Design Characteristics**:
+- **Deterministic**: Tests produce consistent results
+- **Isolated**: No test dependencies or shared state
+- **Fast**: Unit tests complete in milliseconds
+- **Comprehensive**: Edge cases and error conditions covered
+
+## Integration with Development Workflow
+
+### Test-Driven Development Support
+
+**TDD Cycle Integration**:
+1. **Red**: Write failing test for new functionality
+2. **Green**: Implement minimal code to pass test
+3. **Refactor**: Improve code while maintaining test coverage
+
+### Pre-Commit Testing
+
+**Quality Gates**:
+- **Security validation** before commits
+- **Functionality regression** prevention
+- **Code quality** maintenance
+- **Performance baseline** protection
+
+### CI/CD Integration
+
+**GitHub Actions Workflow**:
+- **Multi-Python version** testing (3.10, 3.11, 3.12)
+- **Parallel test execution** for efficiency
+- **Selective live testing** when API keys available
+- **Coverage reporting** and quality gates
+
+## Best Practices Demonstrated
+
+### 1. Comprehensive Mocking
+Every external dependency is properly mocked for reliable testing
+
+### 2. Security-First Approach
+Strong emphasis on security validation and vulnerability prevention
+
+### 3. Collaboration Testing
+Extensive testing of AI-to-AI communication and workflow patterns
+
+### 4. Real-World Scenarios
+Tests cover actual usage patterns and edge cases
+
+### 5. Maintainable Structure
+Clear organization and focused test files for easy maintenance
+
+## Recommendations for Contributors
+
+### Adding New Tests
+
+1. **Follow Naming Conventions**: Use descriptive test names that explain the scenario
+2. **Maintain Isolation**: Mock all external dependencies
+3. **Test Security**: Include path validation and security checks
+4. **Cover Edge Cases**: Test error conditions and boundary cases
+5. **Document Purpose**: Use docstrings to explain test objectives
+
+### Test Quality Standards
+
+1. **Fast Execution**: Unit tests should complete in milliseconds
+2. **Predictable Results**: Tests should be deterministic
+3. **Clear Assertions**: Use descriptive assertion messages
+4. **Proper Cleanup**: Ensure tests don't leave side effects
+
+### Testing New Features
+
+1. **Start with Unit Tests**: Test individual components first
+2. **Add Integration Tests**: Test component interactions
+3. **Include Security Tests**: Validate security measures
+4. **Test Collaboration**: If relevant, test AI-to-AI workflows
+
+---
+
+This test structure demonstrates a mature, production-ready testing approach that ensures code quality, security, and reliability while supporting the collaborative AI development patterns that make this project unique.
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diff --git a/docs/contributing/testing.md b/docs/contributing/testing.md
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--- a/docs/contributing/testing.md
+++ b/docs/contributing/testing.md
@@ -679,6 +679,12 @@ jobs:
           file: ./coverage.xml
 ```
 
+## Detailed Test Structure Analysis
+
+For a comprehensive analysis of the existing test suite, including detailed breakdowns of all 17 test files, security testing patterns, and collaboration feature validation, see:
+
+**[Test Structure Documentation](test-structure.md)** - Complete analysis of existing test organization, mocking strategies, and quality assurance patterns
+
 ---
 
 This comprehensive testing strategy ensures high-quality, reliable code while maintaining development velocity and supporting the collaborative patterns defined in CLAUDE.md.
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