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¶
# 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:
# 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¶
# 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:
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¶
# 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
# 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
# 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)
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:
# 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:
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¶
# 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:
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:
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¶
# 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
# 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
# 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
# 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¶
# 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.