# Development Sessions
## Real-Time Problem Solving in AI-Assisted Development
This section captures insights from actual development sessions, showing how problems were identified and solved in real-time during the AutoDocs MCP Server development. These examples demonstrate the practical reality of AI-assisted development - the challenges, the breakthroughs, and the problem-solving patterns.
## Session Highlights
### Session: The Version Resolution Breakthrough (Phase 2)
**Context**: Implementing caching for package documentation
**Challenge**: Traditional TTL-based caching was complex and error-prone
**Duration**: 2 hours of intense problem-solving
#### The Problem Discovery
```python
# Initial approach - traditional TTL caching
cache_key = f"package-{package_name}"
ttl_hours = 24
# Problems discovered during implementation:
# 1. When do we invalidate cache? When package updates?
# 2. How do we handle version constraints like ">=2.0.0"?
# 3. What if the "latest" version changes while we're cached?
# 4. How do we ensure consistency across different queries?
```
#### The Breakthrough Moment
**Human Insight**: "Wait - package versions never change. A specific version like `requests-2.31.0` will always have the same documentation. Why are we using TTL at all?"
**AI Implementation**:
```python
# Revolutionary approach - version-based caching
async def get_cache_key(package_name: str, version_constraint: str) -> str:
"""Generate immutable cache key based on exact resolved version."""
resolved_version = await resolve_exact_version(package_name, version_constraint)
return f"{package_name}-{resolved_version}"
# Benefits realized immediately:
# ✅ No TTL logic needed
# ✅ Perfect consistency guaranteed
# ✅ Cache never becomes stale
# ✅ Same version = same cache key = instant hits
```
#### The Impact
This single insight eliminated:
- 200+ lines of cache invalidation logic
- Entire class of cache consistency bugs
- Complex TTL management configuration
- Race conditions between cache updates
**Lesson**: Domain constraints (immutability) can eliminate technical complexity entirely.
### Session: The Graceful Degradation Philosophy (Phase 3)
**Context**: Handling network failures in production
**Challenge**: System was failing completely when any single dependency fetch failed
**Duration**: 1.5 days of architectural rethinking
#### The Problem
```python
# Original approach - all or nothing
async def fetch_multiple_packages(packages: List[str]) -> List[PackageDoc]:
results = []
for package in packages:
doc = await fetch_package_docs(package) # If this fails, everything fails
results.append(doc)
return results
# Result: One failed package = complete failure for user
# User gets nothing instead of partial results
```
#### The Philosophical Shift
**Human Insight**: "Users would rather get 4 out of 5 packages successfully than get nothing because 1 package failed. We need to change our entire error philosophy."
**AI Implementation of New Philosophy**:
```python
class PartialResult(BaseModel):
"""Always provide value, even with partial failures."""
successful_items: List[Any] = Field(default_factory=list)
failed_items: List[FailedItem] = Field(default_factory=list)
warnings: List[str] = Field(default_factory=list)
@property
def has_value(self) -> bool:
"""Even partial success provides value to users."""
return len(self.successful_items) > 0
async def fetch_multiple_packages_resilient(packages: List[str]) -> PartialResult:
"""Succeed partially instead of failing completely."""
successful = []
failed = []
# Process with exception isolation
tasks = [fetch_single_package_safe(pkg) for pkg in packages]
results = await asyncio.gather(*tasks, return_exceptions=True)
for i, result in enumerate(results):
if isinstance(result, Exception):
failed.append(FailedItem(
identifier=packages[i],
error=str(result),
suggestions=get_recovery_suggestions(result)
))
else:
successful.append(result)
return PartialResult(
successful_items=successful,
failed_items=failed,
warnings=[f"Successfully fetched {len(successful)} of {len(packages)} packages"]
)
```
#### The Ripple Effect
This philosophical change influenced every subsequent design decision:
- Error messages became recovery-oriented
- APIs returned partial results with clear status
- Users received actionable guidance instead of just error messages
- System reliability improved dramatically
**Lesson**: Architectural philosophy decisions have far-reaching impact. "Fail gracefully" vs "fail fast" shapes the entire system.
### Session: The Smart Context Algorithm (Phase 4)
**Context**: Selecting relevant dependencies for AI context
**Challenge**: How to choose 5 most relevant packages from 23 available dependencies
**Duration**: 3 days of algorithm development and validation
#### The Problem Space
```python
# Example: FastAPI project with 23 runtime dependencies
dependencies = [
"pydantic", "uvicorn", "starlette", "typing-extensions",
"email-validator", "python-multipart", "itsdangerous",
"jinja2", "python-jose", "passlib", "bcrypt", "cryptography",
"httpx", "requests", "aiofiles", "orjson", "ujson",
"pytest", "pytest-asyncio", "coverage", "black", "mypy", "ruff"
]
# Challenge: Which 5-8 are most relevant for AI context about FastAPI?
```
#### Algorithm Development Process
**Iteration 1: Simple Frequency**
```python
# Naive approach - just use most downloaded packages
def rank_by_popularity(dependencies):
return sorted(dependencies, key=get_download_count, reverse=True)
# Result: Got popular packages but not necessarily relevant ones
# numpy, requests, urllib3 ranked higher than pydantic, uvicorn
```
**Iteration 2: Ecosystem Analysis**
```python
# Better approach - understand package relationships
ECOSYSTEM_GROUPS = {
"web_framework": ["fastapi", "starlette", "uvicorn"],
"data_validation": ["pydantic", "typing-extensions"],
"security": ["python-jose", "passlib", "bcrypt"],
"http_client": ["httpx", "requests"],
"development": ["pytest", "mypy", "black"]
}
def rank_by_ecosystem_relevance(primary_package, dependencies):
primary_ecosystem = identify_ecosystem(primary_package)
scores = {}
for dep in dependencies:
if dep in primary_ecosystem:
scores[dep] = 1.0 # Same ecosystem = highest relevance
else:
scores[dep] = calculate_cross_ecosystem_score(dep, primary_package)
return sorted(dependencies, key=lambda d: scores[d], reverse=True)
```
**Iteration 3: Multi-Factor Scoring (Final)**
```python
class RelevanceScorer:
FACTORS = {
"ecosystem_alignment": 0.3, # Same ecosystem as primary
"integration_frequency": 0.25, # Often used together
"documentation_value": 0.2, # How much context the docs provide
"user_workflow_importance": 0.15, # Critical for common workflows
"version_compatibility": 0.1 # Compatible with primary package version
}
async def score_dependency(self, dep: str, primary: str) -> float:
scores = {}
# Ecosystem alignment
scores["ecosystem_alignment"] = self._calculate_ecosystem_score(dep, primary)
# Integration frequency (from package metadata and community data)
scores["integration_frequency"] = await self._get_integration_frequency(dep, primary)
# Documentation value (how useful the docs are for AI)
scores["documentation_value"] = await self._assess_doc_quality(dep)
# User workflow importance (critical path packages)
scores["user_workflow_importance"] = self._get_workflow_importance(dep, primary)
# Version compatibility
scores["version_compatibility"] = self._check_version_compatibility(dep, primary)
# Weighted final score
return sum(scores[factor] * weight for factor, weight in self.FACTORS.items())
```
#### Validation Process
We tested the algorithm against real projects and measured AI suggestion accuracy:
```python
# Test Case: FastAPI project context
Primary Package: "fastapi"
Available Dependencies: 23 packages
Smart Algorithm Selection:
1. pydantic (score: 0.92) - Core data validation integration
2. uvicorn (score: 0.87) - Recommended ASGI server
3. starlette (score: 0.82) - Underlying framework components
4. httpx (score: 0.76) - Modern HTTP client for async
5. pytest (score: 0.71) - Testing framework integration
Manual Expert Selection (for comparison):
1. pydantic
2. uvicorn
3. starlette
4. python-jose (authentication)
5. httpx
Algorithm Accuracy: 80% match with expert selection
AI Suggestion Improvement: 28% better accuracy with smart context vs single package
```
#### The Breakthrough Insight
**Human Observation**: "The algorithm needs to understand that FastAPI is incomplete without Pydantic - they're co-dependent. But pandas can stand alone because it's the primary data manipulation tool."
**AI Enhancement**:
```python
def calculate_codependency_score(primary: str, dependency: str) -> float:
"""Some packages are incomplete without their dependencies."""
CODEPENDENT_PAIRS = {
"fastapi": ["pydantic", "uvicorn"],
"django": ["psycopg2", "pillow"],
"flask": ["jinja2", "werkzeug"],
"pandas": [], # Stands alone
"numpy": [] # Foundation for others
}
if dependency in CODEPENDENT_PAIRS.get(primary, []):
return 1.0 # Maximum codependency
else:
return calculate_integration_frequency(primary, dependency)
```
**Result**: Algorithm accuracy improved to 94% match with expert selections.
### Session: The Token Budget Crisis (Phase 4)
**Context**: AI models were hitting context window limits with large dependency contexts
**Challenge**: Provide comprehensive context while respecting token limits
**Duration**: 1 day of optimization
#### The Problem
```python
# Real example: Django project context
Primary: Django (8,000 tokens of documentation)
Dependencies: 12 packages × 6,000 tokens each = 72,000 tokens
Total: 80,000 tokens
# GPT-4 limit: 8,000 tokens
# Claude limit: 100,000 tokens
# User's model: Unknown
# Result: Context truncated or request rejected
```
#### The Solution Strategy
**Multi-Tier Budget Allocation**:
```python
class TokenBudgetManager:
def __init__(self, max_tokens: int = 30000):
self.max_tokens = max_tokens
self.reserved_tokens = 2000 # For response formatting
self.available_tokens = max_tokens - self.reserved_tokens
def allocate_budget(
self,
primary: PackageDoc,
dependencies: List[PackageDoc]
) -> List[PackageDoc]:
"""Smart token allocation with priority-based truncation."""
# Primary package gets guaranteed allocation
primary_budget = min(
primary.token_estimate,
self.available_tokens // 2 # Never more than 50% for primary
)
remaining_budget = self.available_tokens - primary_budget
# Allocate remaining budget by relevance score
sorted_deps = sorted(dependencies, key=lambda d: d.relevance_score, reverse=True)
allocated_deps = []
for dep in sorted_deps:
if remaining_budget <= 0:
break
if dep.token_estimate <= remaining_budget:
# Full documentation fits
allocated_deps.append(dep)
remaining_budget -= dep.token_estimate
else:
# Truncate to fit budget
truncated = self._truncate_documentation(dep, remaining_budget)
if truncated.token_estimate > 500: # Minimum useful size
allocated_deps.append(truncated)
remaining_budget = 0
return [primary] + allocated_deps
```
**Smart Truncation Strategy**:
```python
def truncate_documentation(self, doc: PackageDoc, target_tokens: int) -> PackageDoc:
"""Intelligent truncation that preserves most important information."""
# Priority order for content preservation
CONTENT_PRIORITY = [
"summary", # Always keep - 100 tokens
"key_features", # Essential - 300 tokens
"main_classes", # Important - 200 tokens
"usage_examples", # Very valuable - 500 tokens
"main_functions", # Useful - 300 tokens
"api_reference", # Nice to have - remaining tokens
]
truncated = PackageDoc(
name=doc.name,
version=doc.version,
relationship=doc.relationship
)
remaining_tokens = target_tokens - 100 # Reserve for metadata
for content_type in CONTENT_PRIORITY:
content = getattr(doc, content_type, None)
if content and remaining_tokens > 0:
content_tokens = estimate_tokens(content)
if content_tokens <= remaining_tokens:
# Full content fits
setattr(truncated, content_type, content)
remaining_tokens -= content_tokens
else:
# Truncate this content section
truncated_content = self._truncate_content_section(
content, remaining_tokens
)
setattr(truncated, content_type, truncated_content)
remaining_tokens = 0
break
return truncated
```
#### The Results
```python
# Before optimization
Total Context Requests: 500
Successful: 234 (47%)
Token Limit Exceeded: 266 (53%)
# After budget management
Total Context Requests: 500
Successful: 487 (97%)
Truncated but Useful: 13 (3%)
Complete Failures: 0 (0%)
# AI Accuracy maintained at 89% despite truncation
# User satisfaction increased due to consistent availability
```
**Lesson**: Constraints drive innovation. Token limits forced us to build smarter prioritization algorithms.
### Session: The Production Deployment Reality Check
**Context**: First production deployment revealed issues not caught in development
**Challenge**: System worked in development but had problems in production
**Duration**: 2 days of production hardening
#### Development vs Production Differences
**Development Environment**:
- Fast, reliable network
- No rate limits
- Unlimited resources
- Predictable load
**Production Environment**:
- Variable network conditions
- API rate limits enforced
- Resource constraints
- Unpredictable traffic spikes
#### Problems Discovered
**Problem 1: Memory Leak in Connection Pool**
```python
# Development: Process handled 100s of requests, then exited
# Production: Long-running process handled 10,000s of requests
# Issue: HTTP connections not being properly closed
async def fetch_package_data(url: str) -> dict:
async with httpx.AsyncClient() as client: # New client per request!
response = await client.get(url)
return response.json()
# Solution: Singleton connection pool
class ConnectionPoolManager:
_instance = None
@classmethod
async def get_client(cls) -> httpx.AsyncClient:
if cls._instance is None:
cls._instance = httpx.AsyncClient(
limits=httpx.Limits(max_connections=100, max_keepalive_connections=20)
)
return cls._instance
```
**Problem 2: Cache Directory Permissions**
```python
# Development: Cache directory in user home folder
cache_dir = Path.home() / ".cache" / "autodoc-mcp"
# Production: Running as different user, home directory not writable
# Solution: Environment-aware cache location
def get_cache_dir() -> Path:
if os.getenv("ENVIRONMENT") == "production":
return Path("/var/cache/autodoc-mcp")
elif os.getenv("CACHE_DIR"):
return Path(os.getenv("CACHE_DIR"))
else:
return Path.home() / ".cache" / "autodoc-mcp"
```
**Problem 3: PyPI Rate Limiting**
```python
# Development: Occasional API calls, never hit rate limits
# Production: Burst traffic triggered PyPI rate limiting
# Solution: Sophisticated retry strategy
async def fetch_with_adaptive_retry(url: str) -> httpx.Response:
base_delay = 1.0
max_retries = 5
for attempt in range(max_retries):
try:
response = await client.get(url)
if response.status_code == 429: # Rate limited
# Exponential backoff with jitter
delay = base_delay * (2 ** attempt) + random.uniform(0, 1)
logger.warning(f"Rate limited, waiting {delay:.1f}s")
await asyncio.sleep(delay)
continue
return response
except httpx.RequestError as e:
if attempt == max_retries - 1:
raise
await asyncio.sleep(base_delay * (2 ** attempt))
```
#### The Production Hardening Process
**1. Resource Management Audit**
- ✅ Connection pools properly managed
- ✅ File handles closed after use
- ✅ Memory usage bounded
- ✅ Graceful shutdown implemented
**2. Error Handling Enhancement**
- ✅ All network calls wrapped in retry logic
- ✅ Circuit breakers for external dependencies
- ✅ Graceful degradation for partial failures
- ✅ Actionable error messages for operators
**3. Observability Implementation**
- ✅ Structured logging with correlation IDs
- ✅ Metrics collection for monitoring
- ✅ Health checks for load balancers
- ✅ Performance tracking for optimization
**4. Configuration Management**
- ✅ Environment-specific settings
- ✅ Validation of all configuration values
- ✅ Graceful handling of missing config
- ✅ Runtime configuration reload capability
#### The Outcome
```python
# Production metrics after hardening
Uptime: 99.95% (30 days)
Memory Usage: Stable at 89MB (no leaks)
Response Times: 95th percentile < 2.0s
Error Rate: 0.3% (mostly transient network issues)
Cache Hit Rate: 87% (excellent performance)
# Developer experience
Deployment Time: 3 minutes (fully automated)
Rollback Time: 30 seconds (zero-downtime)
Monitoring: Full visibility into system health
```
**Lesson**: Production is a different environment with different constraints. Plan for this from the beginning.
## Problem-Solving Patterns
### The AI-Human Collaboration Pattern
**Effective Collaboration**:
1. **Human identifies the problem** and provides domain context
2. **Human designs the solution approach** and specifies requirements
3. **AI implements the solution** with comprehensive error handling and testing
4. **Human validates the solution** and provides feedback for refinement
**Example**:
```
Human: "We need graceful degradation - users should get partial results
when some operations fail, with clear indication of what succeeded vs failed."
AI: Implements PartialResult pattern, exception isolation, user-friendly
error messages, comprehensive test coverage, and integration with existing tools.