From cbb60494b1df88ff43bff46821df5e71af6883c7 Mon Sep 17 00:00:00 2001
From: "M. A." <49915873+mohammadaffaneh@users.noreply.github.com>
Date: Fri, 30 Jan 2026 17:52:14 +0100
Subject: [PATCH] Add Comprehensive Python Development Skills (#419)

* Add extra python skills covering code style, design patterns, resilience, resource management, testing patterns, and type safety ...etc

* fix: correct code examples in Python skills

- Clarify Python version requirements for type statement (3.10+ vs 3.12+)
- Add missing ValidationError import in configuration example
- Add missing httpx import and url parameter in async example

---------

Co-authored-by: Seth Hobson <wshobson@gmail.com>
---
 .claude-plugin/marketplace.json               |  15 +-
 README.md                                     |   6 +-
 .../skills/async-python-patterns/SKILL.md     |  65 ++-
 .../skills/python-anti-patterns/SKILL.md      | 349 ++++++++++++++
 .../skills/python-background-jobs/SKILL.md    | 364 +++++++++++++++
 .../skills/python-code-style/SKILL.md         | 360 +++++++++++++++
 .../skills/python-configuration/SKILL.md      | 368 +++++++++++++++
 .../skills/python-design-patterns/SKILL.md    | 411 +++++++++++++++++
 .../skills/python-error-handling/SKILL.md     | 359 +++++++++++++++
 .../skills/python-observability/SKILL.md      | 400 ++++++++++++++++
 .../skills/python-project-structure/SKILL.md  | 252 +++++++++++
 .../skills/python-resilience/SKILL.md         | 376 +++++++++++++++
 .../python-resource-management/SKILL.md       | 421 +++++++++++++++++
 .../skills/python-testing-patterns/SKILL.md   | 155 ++++++-
 .../skills/python-type-safety/SKILL.md        | 428 ++++++++++++++++++
 15 files changed, 4311 insertions(+), 18 deletions(-)
 create mode 100644 plugins/python-development/skills/python-anti-patterns/SKILL.md
 create mode 100644 plugins/python-development/skills/python-background-jobs/SKILL.md
 create mode 100644 plugins/python-development/skills/python-code-style/SKILL.md
 create mode 100644 plugins/python-development/skills/python-configuration/SKILL.md
 create mode 100644 plugins/python-development/skills/python-design-patterns/SKILL.md
 create mode 100644 plugins/python-development/skills/python-error-handling/SKILL.md
 create mode 100644 plugins/python-development/skills/python-observability/SKILL.md
 create mode 100644 plugins/python-development/skills/python-project-structure/SKILL.md
 create mode 100644 plugins/python-development/skills/python-resilience/SKILL.md
 create mode 100644 plugins/python-development/skills/python-resource-management/SKILL.md
 create mode 100644 plugins/python-development/skills/python-type-safety/SKILL.md

diff --git a/.claude-plugin/marketplace.json b/.claude-plugin/marketplace.json
index c114ed9..dc553f4 100644
--- a/.claude-plugin/marketplace.json
+++ b/.claude-plugin/marketplace.json
@@ -6,7 +6,7 @@
     "url": "https://github.com/wshobson"
   },
   "metadata": {
-    "description": "Production-ready workflow orchestration with 72 focused plugins, 108 specialized agents, and 129 skills - optimized for granular installation and minimal token usage",
+    "description": "Production-ready workflow orchestration with 72 focused plugins, 108 specialized agents, and 140 skills - optimized for granular installation and minimal token usage",
     "version": "1.3.7"
   },
   "plugins": [
@@ -1611,7 +1611,18 @@
         "./skills/python-testing-patterns",
         "./skills/python-packaging",
         "./skills/python-performance-optimization",
-        "./skills/uv-package-manager"
+        "./skills/uv-package-manager",
+        "./skills/python-type-safety",
+        "./skills/python-code-style",
+        "./skills/python-observability",
+        "./skills/python-project-structure",
+        "./skills/python-design-patterns",
+        "./skills/python-error-handling",
+        "./skills/python-configuration",
+        "./skills/python-resilience",
+        "./skills/python-resource-management",
+        "./skills/python-background-jobs",
+        "./skills/python-anti-patterns"
       ]
     },
     {
diff --git a/README.md b/README.md
index f41ab9a..e51ecab 100644
--- a/README.md
+++ b/README.md
@@ -37,7 +37,7 @@ Each plugin is completely isolated with its own agents, commands, and skills:
 - **Clear boundaries** - Each plugin has a single, focused purpose
 - **Progressive disclosure** - Skills load knowledge only when activated
 
-**Example**: Installing `python-development` loads 3 Python agents, 1 scaffolding tool, and makes 5 skills available (~300 tokens), not the entire marketplace.
+**Example**: Installing `python-development` loads 3 Python agents, 1 scaffolding tool, and makes 16 skills available (~1000 tokens), not the entire marketplace.
 
 ## Quick Start
 
@@ -63,7 +63,7 @@ Install the plugins you need:
 
 ```bash
 # Essential development plugins
-/plugin install python-development          # Python with 5 specialized skills
+/plugin install python-development          # Python with 16 specialized skills
 /plugin install javascript-typescript       # JS/TS with 4 specialized skills
 /plugin install backend-development         # Backend APIs with 3 architecture skills
 
@@ -130,7 +130,7 @@ rm -rf ~/.claude/plugins/cache/claude-code-workflows && rm ~/.claude/plugins/ins
 
 ## What's New
 
-### Agent Skills (129 skills across 20 plugins)
+### Agent Skills (140 skills across 20 plugins)
 
 Specialized knowledge packages following Anthropic's progressive disclosure architecture:
 
diff --git a/plugins/python-development/skills/async-python-patterns/SKILL.md b/plugins/python-development/skills/async-python-patterns/SKILL.md
index 9504ce4..78c8f1e 100644
--- a/plugins/python-development/skills/async-python-patterns/SKILL.md
+++ b/plugins/python-development/skills/async-python-patterns/SKILL.md
@@ -18,6 +18,20 @@ Comprehensive guidance for implementing asynchronous Python applications using a
 - Optimizing I/O-bound workloads
 - Implementing async background tasks and queues
 
+## Sync vs Async Decision Guide
+
+Before adopting async, consider whether it's the right choice for your use case.
+
+| Use Case | Recommended Approach |
+|----------|---------------------|
+| Many concurrent network/DB calls | `asyncio` |
+| CPU-bound computation | `multiprocessing` or thread pool |
+| Mixed I/O + CPU | Offload CPU work with `asyncio.to_thread()` |
+| Simple scripts, few connections | Sync (simpler, easier to debug) |
+| Web APIs with high concurrency | Async frameworks (FastAPI, aiohttp) |
+
+**Key Rule:** Stay fully sync or fully async within a call path. Mixing creates hidden blocking and complexity.
+
 ## Core Concepts
 
 ### 1. Event Loop
@@ -583,6 +597,46 @@ async def process_item(item: str):
 
 ### 3. Avoid Blocking Operations
 
+Never block the event loop with synchronous operations. A single blocking call stalls all concurrent tasks.
+
+```python
+# BAD - blocks the entire event loop
+async def fetch_data_bad():
+    import time
+    import requests
+    time.sleep(1)  # Blocks!
+    response = requests.get(url)  # Also blocks!
+
+# GOOD - use async-native libraries (e.g., httpx for async HTTP)
+import httpx
+
+async def fetch_data_good(url: str):
+    await asyncio.sleep(1)
+    async with httpx.AsyncClient() as client:
+        response = await client.get(url)
+```
+
+**Wrapping Blocking Code with `asyncio.to_thread()` (Python 3.9+):**
+
+When you must use synchronous libraries, offload to a thread pool:
+
+```python
+import asyncio
+from pathlib import Path
+
+async def read_file_async(path: str) -> str:
+    """Read file without blocking event loop."""
+    # asyncio.to_thread() runs sync code in a thread pool
+    return await asyncio.to_thread(Path(path).read_text)
+
+async def call_sync_library(data: dict) -> dict:
+    """Wrap a synchronous library call."""
+    # Useful for sync database drivers, file I/O, CPU work
+    return await asyncio.to_thread(sync_library.process, data)
+```
+
+**Lower-level approach with `run_in_executor()`:**
+
 ```python
 import asyncio
 import concurrent.futures
@@ -596,7 +650,7 @@ def blocking_operation(data: Any) -> Any:
 
 async def run_in_executor(data: Any) -> Any:
     """Run blocking operation in thread pool."""
-    loop = asyncio.get_event_loop()
+    loop = asyncio.get_running_loop()
     with concurrent.futures.ThreadPoolExecutor() as pool:
         result = await loop.run_in_executor(pool, blocking_operation, data)
         return result
@@ -692,11 +746,12 @@ async def test_with_timeout():
 
 1. **Use asyncio.run()** for entry point (Python 3.7+)
 2. **Always await coroutines** to execute them
-3. **Use gather() for concurrent execution** of multiple tasks
+3. **Limit concurrency with semaphores** - unbounded `gather()` can exhaust resources
 4. **Implement proper error handling** with try/except
 5. **Use timeouts** to prevent hanging operations
 6. **Pool connections** for better performance
-7. **Avoid blocking operations** in async code
-8. **Use semaphores** for rate limiting
-9. **Handle task cancellation** properly
+7. **Never block the event loop** - use `asyncio.to_thread()` for sync code
+8. **Use semaphores** for rate limiting external API calls
+9. **Handle task cancellation** properly - always re-raise `CancelledError`
 10. **Test async code** with pytest-asyncio
+11. **Stay consistent** - fully sync or fully async, avoid mixing
diff --git a/plugins/python-development/skills/python-anti-patterns/SKILL.md b/plugins/python-development/skills/python-anti-patterns/SKILL.md
new file mode 100644
index 0000000..963a67d
--- /dev/null
+++ b/plugins/python-development/skills/python-anti-patterns/SKILL.md
@@ -0,0 +1,349 @@
+---
+name: python-anti-patterns
+description: Common Python anti-patterns to avoid. Use as a checklist when reviewing code, before finalizing implementations, or when debugging issues that might stem from known bad practices.
+---
+
+# Python Anti-Patterns Checklist
+
+A reference checklist of common mistakes and anti-patterns in Python code. Review this before finalizing implementations to catch issues early.
+
+## When to Use This Skill
+
+- Reviewing code before merge
+- Debugging mysterious issues
+- Teaching or learning Python best practices
+- Establishing team coding standards
+- Refactoring legacy code
+
+**Note:** This skill focuses on what to avoid. For guidance on positive patterns and architecture, see the `python-design-patterns` skill.
+
+## Infrastructure Anti-Patterns
+
+### Scattered Timeout/Retry Logic
+
+```python
+# BAD: Timeout logic duplicated everywhere
+def fetch_user(user_id):
+    try:
+        return requests.get(url, timeout=30)
+    except Timeout:
+        logger.warning("Timeout fetching user")
+        return None
+
+def fetch_orders(user_id):
+    try:
+        return requests.get(url, timeout=30)
+    except Timeout:
+        logger.warning("Timeout fetching orders")
+        return None
+```
+
+**Fix:** Centralize in decorators or client wrappers.
+
+```python
+# GOOD: Centralized retry logic
+@retry(stop=stop_after_attempt(3), wait=wait_exponential())
+def http_get(url: str) -> Response:
+    return requests.get(url, timeout=30)
+```
+
+### Double Retry
+
+```python
+# BAD: Retrying at multiple layers
+@retry(max_attempts=3)  # Application retry
+def call_service():
+    return client.request()  # Client also has retry configured!
+```
+
+**Fix:** Retry at one layer only. Know your infrastructure's retry behavior.
+
+### Hard-Coded Configuration
+
+```python
+# BAD: Secrets and config in code
+DB_HOST = "prod-db.example.com"
+API_KEY = "sk-12345"
+
+def connect():
+    return psycopg.connect(f"host={DB_HOST}...")
+```
+
+**Fix:** Use environment variables with typed settings.
+
+```python
+# GOOD
+from pydantic_settings import BaseSettings
+
+class Settings(BaseSettings):
+    db_host: str = Field(alias="DB_HOST")
+    api_key: str = Field(alias="API_KEY")
+
+settings = Settings()
+```
+
+## Architecture Anti-Patterns
+
+### Exposed Internal Types
+
+```python
+# BAD: Leaking ORM model to API
+@app.get("/users/{id}")
+def get_user(id: str) -> UserModel:  # SQLAlchemy model
+    return db.query(UserModel).get(id)
+```
+
+**Fix:** Use DTOs/response models.
+
+```python
+# GOOD
+@app.get("/users/{id}")
+def get_user(id: str) -> UserResponse:
+    user = db.query(UserModel).get(id)
+    return UserResponse.from_orm(user)
+```
+
+### Mixed I/O and Business Logic
+
+```python
+# BAD: SQL embedded in business logic
+def calculate_discount(user_id: str) -> float:
+    user = db.query("SELECT * FROM users WHERE id = ?", user_id)
+    orders = db.query("SELECT * FROM orders WHERE user_id = ?", user_id)
+    # Business logic mixed with data access
+    if len(orders) > 10:
+        return 0.15
+    return 0.0
+```
+
+**Fix:** Repository pattern. Keep business logic pure.
+
+```python
+# GOOD
+def calculate_discount(user: User, orders: list[Order]) -> float:
+    # Pure business logic, easily testable
+    if len(orders) > 10:
+        return 0.15
+    return 0.0
+```
+
+## Error Handling Anti-Patterns
+
+### Bare Exception Handling
+
+```python
+# BAD: Swallowing all exceptions
+try:
+    process()
+except Exception:
+    pass  # Silent failure - bugs hidden forever
+```
+
+**Fix:** Catch specific exceptions. Log or handle appropriately.
+
+```python
+# GOOD
+try:
+    process()
+except ConnectionError as e:
+    logger.warning("Connection failed, will retry", error=str(e))
+    raise
+except ValueError as e:
+    logger.error("Invalid input", error=str(e))
+    raise BadRequestError(str(e))
+```
+
+### Ignored Partial Failures
+
+```python
+# BAD: Stops on first error
+def process_batch(items):
+    results = []
+    for item in items:
+        result = process(item)  # Raises on error - batch aborted
+        results.append(result)
+    return results
+```
+
+**Fix:** Capture both successes and failures.
+
+```python
+# GOOD
+def process_batch(items) -> BatchResult:
+    succeeded = {}
+    failed = {}
+    for idx, item in enumerate(items):
+        try:
+            succeeded[idx] = process(item)
+        except Exception as e:
+            failed[idx] = e
+    return BatchResult(succeeded, failed)
+```
+
+### Missing Input Validation
+
+```python
+# BAD: No validation
+def create_user(data: dict):
+    return User(**data)  # Crashes deep in code on bad input
+```
+
+**Fix:** Validate early at API boundaries.
+
+```python
+# GOOD
+def create_user(data: dict) -> User:
+    validated = CreateUserInput.model_validate(data)
+    return User.from_input(validated)
+```
+
+## Resource Anti-Patterns
+
+### Unclosed Resources
+
+```python
+# BAD: File never closed
+def read_file(path):
+    f = open(path)
+    return f.read()  # What if this raises?
+```
+
+**Fix:** Use context managers.
+
+```python
+# GOOD
+def read_file(path):
+    with open(path) as f:
+        return f.read()
+```
+
+### Blocking in Async
+
+```python
+# BAD: Blocks the entire event loop
+async def fetch_data():
+    time.sleep(1)  # Blocks everything!
+    response = requests.get(url)  # Also blocks!
+```
+
+**Fix:** Use async-native libraries.
+
+```python
+# GOOD
+async def fetch_data():
+    await asyncio.sleep(1)
+    async with httpx.AsyncClient() as client:
+        response = await client.get(url)
+```
+
+## Type Safety Anti-Patterns
+
+### Missing Type Hints
+
+```python
+# BAD: No types
+def process(data):
+    return data["value"] * 2
+```
+
+**Fix:** Annotate all public functions.
+
+```python
+# GOOD
+def process(data: dict[str, int]) -> int:
+    return data["value"] * 2
+```
+
+### Untyped Collections
+
+```python
+# BAD: Generic list without type parameter
+def get_users() -> list:
+    ...
+```
+
+**Fix:** Use type parameters.
+
+```python
+# GOOD
+def get_users() -> list[User]:
+    ...
+```
+
+## Testing Anti-Patterns
+
+### Only Testing Happy Paths
+
+```python
+# BAD: Only tests success case
+def test_create_user():
+    user = service.create_user(valid_data)
+    assert user.id is not None
+```
+
+**Fix:** Test error conditions and edge cases.
+
+```python
+# GOOD
+def test_create_user_success():
+    user = service.create_user(valid_data)
+    assert user.id is not None
+
+def test_create_user_invalid_email():
+    with pytest.raises(ValueError, match="Invalid email"):
+        service.create_user(invalid_email_data)
+
+def test_create_user_duplicate_email():
+    service.create_user(valid_data)
+    with pytest.raises(ConflictError):
+        service.create_user(valid_data)
+```
+
+### Over-Mocking
+
+```python
+# BAD: Mocking everything
+def test_user_service():
+    mock_repo = Mock()
+    mock_cache = Mock()
+    mock_logger = Mock()
+    mock_metrics = Mock()
+    # Test doesn't verify real behavior
+```
+
+**Fix:** Use integration tests for critical paths. Mock only external services.
+
+## Quick Review Checklist
+
+Before finalizing code, verify:
+
+- [ ] No scattered timeout/retry logic (centralized)
+- [ ] No double retry (app + infrastructure)
+- [ ] No hard-coded configuration or secrets
+- [ ] No exposed internal types (ORM models, protobufs)
+- [ ] No mixed I/O and business logic
+- [ ] No bare `except Exception: pass`
+- [ ] No ignored partial failures in batches
+- [ ] No missing input validation
+- [ ] No unclosed resources (using context managers)
+- [ ] No blocking calls in async code
+- [ ] All public functions have type hints
+- [ ] Collections have type parameters
+- [ ] Error paths are tested
+- [ ] Edge cases are covered
+
+## Common Fixes Summary
+
+| Anti-Pattern | Fix |
+|-------------|-----|
+| Scattered retry logic | Centralized decorators |
+| Hard-coded config | Environment variables + pydantic-settings |
+| Exposed ORM models | DTO/response schemas |
+| Mixed I/O + logic | Repository pattern |
+| Bare except | Catch specific exceptions |
+| Batch stops on error | Return BatchResult with successes/failures |
+| No validation | Validate at boundaries with Pydantic |
+| Unclosed resources | Context managers |
+| Blocking in async | Async-native libraries |
+| Missing types | Type annotations on all public APIs |
+| Only happy path tests | Test errors and edge cases |
diff --git a/plugins/python-development/skills/python-background-jobs/SKILL.md b/plugins/python-development/skills/python-background-jobs/SKILL.md
new file mode 100644
index 0000000..87218ee
--- /dev/null
+++ b/plugins/python-development/skills/python-background-jobs/SKILL.md
@@ -0,0 +1,364 @@
+---
+name: python-background-jobs
+description: Python background job patterns including task queues, workers, and event-driven architecture. Use when implementing async task processing, job queues, long-running operations, or decoupling work from request/response cycles.
+---
+
+# Python Background Jobs & Task Queues
+
+Decouple long-running or unreliable work from request/response cycles. Return immediately to the user while background workers handle the heavy lifting asynchronously.
+
+## When to Use This Skill
+
+- Processing tasks that take longer than a few seconds
+- Sending emails, notifications, or webhooks
+- Generating reports or exporting data
+- Processing uploads or media transformations
+- Integrating with unreliable external services
+- Building event-driven architectures
+
+## Core Concepts
+
+### 1. Task Queue Pattern
+
+API accepts request, enqueues a job, returns immediately with a job ID. Workers process jobs asynchronously.
+
+### 2. Idempotency
+
+Tasks may be retried on failure. Design for safe re-execution.
+
+### 3. Job State Machine
+
+Jobs transition through states: pending → running → succeeded/failed.
+
+### 4. At-Least-Once Delivery
+
+Most queues guarantee at-least-once delivery. Your code must handle duplicates.
+
+## Quick Start
+
+This skill uses Celery for examples, a widely adopted task queue. Alternatives like RQ, Dramatiq, and cloud-native solutions (AWS SQS, GCP Tasks) are equally valid choices.
+
+```python
+from celery import Celery
+
+app = Celery("tasks", broker="redis://localhost:6379")
+
+@app.task
+def send_email(to: str, subject: str, body: str) -> None:
+    # This runs in a background worker
+    email_client.send(to, subject, body)
+
+# In your API handler
+send_email.delay("user@example.com", "Welcome!", "Thanks for signing up")
+```
+
+## Fundamental Patterns
+
+### Pattern 1: Return Job ID Immediately
+
+For operations exceeding a few seconds, return a job ID and process asynchronously.
+
+```python
+from uuid import uuid4
+from dataclasses import dataclass
+from enum import Enum
+from datetime import datetime
+
+class JobStatus(Enum):
+    PENDING = "pending"
+    RUNNING = "running"
+    SUCCEEDED = "succeeded"
+    FAILED = "failed"
+
+@dataclass
+class Job:
+    id: str
+    status: JobStatus
+    created_at: datetime
+    started_at: datetime | None = None
+    completed_at: datetime | None = None
+    result: dict | None = None
+    error: str | None = None
+
+# API endpoint
+async def start_export(request: ExportRequest) -> JobResponse:
+    """Start export job and return job ID."""
+    job_id = str(uuid4())
+
+    # Persist job record
+    await jobs_repo.create(Job(
+        id=job_id,
+        status=JobStatus.PENDING,
+        created_at=datetime.utcnow(),
+    ))
+
+    # Enqueue task for background processing
+    await task_queue.enqueue(
+        "export_data",
+        job_id=job_id,
+        params=request.model_dump(),
+    )
+
+    # Return immediately with job ID
+    return JobResponse(
+        job_id=job_id,
+        status="pending",
+        poll_url=f"/jobs/{job_id}",
+    )
+```
+
+### Pattern 2: Celery Task Configuration
+
+Configure Celery tasks with proper retry and timeout settings.
+
+```python
+from celery import Celery
+
+app = Celery("tasks", broker="redis://localhost:6379")
+
+# Global configuration
+app.conf.update(
+    task_time_limit=3600,          # Hard limit: 1 hour
+    task_soft_time_limit=3000,      # Soft limit: 50 minutes
+    task_acks_late=True,            # Acknowledge after completion
+    task_reject_on_worker_lost=True,
+    worker_prefetch_multiplier=1,   # Don't prefetch too many tasks
+)
+
+@app.task(
+    bind=True,
+    max_retries=3,
+    default_retry_delay=60,
+    autoretry_for=(ConnectionError, TimeoutError),
+)
+def process_payment(self, payment_id: str) -> dict:
+    """Process payment with automatic retry on transient errors."""
+    try:
+        result = payment_gateway.charge(payment_id)
+        return {"status": "success", "transaction_id": result.id}
+    except PaymentDeclinedError as e:
+        # Don't retry permanent failures
+        return {"status": "declined", "reason": str(e)}
+    except TransientError as e:
+        # Retry with exponential backoff
+        raise self.retry(exc=e, countdown=2 ** self.request.retries * 60)
+```
+
+### Pattern 3: Make Tasks Idempotent
+
+Workers may retry on crash or timeout. Design for safe re-execution.
+
+```python
+@app.task(bind=True)
+def process_order(self, order_id: str) -> None:
+    """Process order idempotently."""
+    order = orders_repo.get(order_id)
+
+    # Already processed? Return early
+    if order.status == OrderStatus.COMPLETED:
+        logger.info("Order already processed", order_id=order_id)
+        return
+
+    # Already in progress? Check if we should continue
+    if order.status == OrderStatus.PROCESSING:
+        # Use idempotency key to avoid double-charging
+        pass
+
+    # Process with idempotency key
+    result = payment_provider.charge(
+        amount=order.total,
+        idempotency_key=f"order-{order_id}",  # Critical!
+    )
+
+    orders_repo.update(order_id, status=OrderStatus.COMPLETED)
+```
+
+**Idempotency Strategies:**
+
+1. **Check-before-write**: Verify state before action
+2. **Idempotency keys**: Use unique tokens with external services
+3. **Upsert patterns**: `INSERT ... ON CONFLICT UPDATE`
+4. **Deduplication window**: Track processed IDs for N hours
+
+### Pattern 4: Job State Management
+
+Persist job state transitions for visibility and debugging.
+
+```python
+class JobRepository:
+    """Repository for managing job state."""
+
+    async def create(self, job: Job) -> Job:
+        """Create new job record."""
+        await self._db.execute(
+            """INSERT INTO jobs (id, status, created_at)
+               VALUES ($1, $2, $3)""",
+            job.id, job.status.value, job.created_at,
+        )
+        return job
+
+    async def update_status(
+        self,
+        job_id: str,
+        status: JobStatus,
+        **fields,
+    ) -> None:
+        """Update job status with timestamp."""
+        updates = {"status": status.value, **fields}
+
+        if status == JobStatus.RUNNING:
+            updates["started_at"] = datetime.utcnow()
+        elif status in (JobStatus.SUCCEEDED, JobStatus.FAILED):
+            updates["completed_at"] = datetime.utcnow()
+
+        await self._db.execute(
+            "UPDATE jobs SET status = $1, ... WHERE id = $2",
+            updates, job_id,
+        )
+
+        logger.info(
+            "Job status updated",
+            job_id=job_id,
+            status=status.value,
+        )
+```
+
+## Advanced Patterns
+
+### Pattern 5: Dead Letter Queue
+
+Handle permanently failed tasks for manual inspection.
+
+```python
+@app.task(bind=True, max_retries=3)
+def process_webhook(self, webhook_id: str, payload: dict) -> None:
+    """Process webhook with DLQ for failures."""
+    try:
+        result = send_webhook(payload)
+        if not result.success:
+            raise WebhookFailedError(result.error)
+    except Exception as e:
+        if self.request.retries >= self.max_retries:
+            # Move to dead letter queue for manual inspection
+            dead_letter_queue.send({
+                "task": "process_webhook",
+                "webhook_id": webhook_id,
+                "payload": payload,
+                "error": str(e),
+                "attempts": self.request.retries + 1,
+                "failed_at": datetime.utcnow().isoformat(),
+            })
+            logger.error(
+                "Webhook moved to DLQ after max retries",
+                webhook_id=webhook_id,
+                error=str(e),
+            )
+            return
+
+        # Exponential backoff retry
+        raise self.retry(exc=e, countdown=2 ** self.request.retries * 60)
+```
+
+### Pattern 6: Status Polling Endpoint
+
+Provide an endpoint for clients to check job status.
+
+```python
+from fastapi import FastAPI, HTTPException
+
+app = FastAPI()
+
+@app.get("/jobs/{job_id}")
+async def get_job_status(job_id: str) -> JobStatusResponse:
+    """Get current status of a background job."""
+    job = await jobs_repo.get(job_id)
+
+    if job is None:
+        raise HTTPException(404, f"Job {job_id} not found")
+
+    return JobStatusResponse(
+        job_id=job.id,
+        status=job.status.value,
+        created_at=job.created_at,
+        started_at=job.started_at,
+        completed_at=job.completed_at,
+        result=job.result if job.status == JobStatus.SUCCEEDED else None,
+        error=job.error if job.status == JobStatus.FAILED else None,
+        # Helpful for clients
+        is_terminal=job.status in (JobStatus.SUCCEEDED, JobStatus.FAILED),
+    )
+```
+
+### Pattern 7: Task Chaining and Workflows
+
+Compose complex workflows from simple tasks.
+
+```python
+from celery import chain, group, chord
+
+# Simple chain: A → B → C
+workflow = chain(
+    extract_data.s(source_id),
+    transform_data.s(),
+    load_data.s(destination_id),
+)
+
+# Parallel execution: A, B, C all at once
+parallel = group(
+    send_email.s(user_email),
+    send_sms.s(user_phone),
+    update_analytics.s(event_data),
+)
+
+# Chord: Run tasks in parallel, then a callback
+# Process all items, then send completion notification
+workflow = chord(
+    [process_item.s(item_id) for item_id in item_ids],
+    send_completion_notification.s(batch_id),
+)
+
+workflow.apply_async()
+```
+
+### Pattern 8: Alternative Task Queues
+
+Choose the right tool for your needs.
+
+**RQ (Redis Queue)**: Simple, Redis-based
+```python
+from rq import Queue
+from redis import Redis
+
+queue = Queue(connection=Redis())
+job = queue.enqueue(send_email, "user@example.com", "Subject", "Body")
+```
+
+**Dramatiq**: Modern Celery alternative
+```python
+import dramatiq
+from dramatiq.brokers.redis import RedisBroker
+
+dramatiq.set_broker(RedisBroker())
+
+@dramatiq.actor
+def send_email(to: str, subject: str, body: str) -> None:
+    email_client.send(to, subject, body)
+```
+
+**Cloud-native options:**
+- AWS SQS + Lambda
+- Google Cloud Tasks
+- Azure Functions
+
+## Best Practices Summary
+
+1. **Return immediately** - Don't block requests for long operations
+2. **Persist job state** - Enable status polling and debugging
+3. **Make tasks idempotent** - Safe to retry on any failure
+4. **Use idempotency keys** - For external service calls
+5. **Set timeouts** - Both soft and hard limits
+6. **Implement DLQ** - Capture permanently failed tasks
+7. **Log transitions** - Track job state changes
+8. **Retry appropriately** - Exponential backoff for transient errors
+9. **Don't retry permanent failures** - Validation errors, invalid credentials
+10. **Monitor queue depth** - Alert on backlog growth
diff --git a/plugins/python-development/skills/python-code-style/SKILL.md b/plugins/python-development/skills/python-code-style/SKILL.md
new file mode 100644
index 0000000..61cf0ba
--- /dev/null
+++ b/plugins/python-development/skills/python-code-style/SKILL.md
@@ -0,0 +1,360 @@
+---
+name: python-code-style
+description: Python code style, linting, formatting, naming conventions, and documentation standards. Use when writing new code, reviewing style, configuring linters, writing docstrings, or establishing project standards.
+---
+
+# Python Code Style & Documentation
+
+Consistent code style and clear documentation make codebases maintainable and collaborative. This skill covers modern Python tooling, naming conventions, and documentation standards.
+
+## When to Use This Skill
+
+- Setting up linting and formatting for a new project
+- Writing or reviewing docstrings
+- Establishing team coding standards
+- Configuring ruff, mypy, or pyright
+- Reviewing code for style consistency
+- Creating project documentation
+
+## Core Concepts
+
+### 1. Automated Formatting
+
+Let tools handle formatting debates. Configure once, enforce automatically.
+
+### 2. Consistent Naming
+
+Follow PEP 8 conventions with meaningful, descriptive names.
+
+### 3. Documentation as Code
+
+Docstrings should be maintained alongside the code they describe.
+
+### 4. Type Annotations
+
+Modern Python code should include type hints for all public APIs.
+
+## Quick Start
+
+```bash
+# Install modern tooling
+pip install ruff mypy
+
+# Configure in pyproject.toml
+[tool.ruff]
+line-length = 120
+target-version = "py312"  # Adjust based on your project's minimum Python version
+
+[tool.mypy]
+strict = true
+```
+
+## Fundamental Patterns
+
+### Pattern 1: Modern Python Tooling
+
+Use `ruff` as an all-in-one linter and formatter. It replaces flake8, isort, and black with a single fast tool.
+
+```toml
+# pyproject.toml
+[tool.ruff]
+line-length = 120
+target-version = "py312"  # Adjust based on your project's minimum Python version
+
+[tool.ruff.lint]
+select = [
+    "E",    # pycodestyle errors
+    "W",    # pycodestyle warnings
+    "F",    # pyflakes
+    "I",    # isort
+    "B",    # flake8-bugbear
+    "C4",   # flake8-comprehensions
+    "UP",   # pyupgrade
+    "SIM",  # flake8-simplify
+]
+ignore = ["E501"]  # Line length handled by formatter
+
+[tool.ruff.format]
+quote-style = "double"
+indent-style = "space"
+```
+
+Run with:
+
+```bash
+ruff check --fix .  # Lint and auto-fix
+ruff format .       # Format code
+```
+
+### Pattern 2: Type Checking Configuration
+
+Configure strict type checking for production code.
+
+```toml
+# pyproject.toml
+[tool.mypy]
+python_version = "3.12"
+strict = true
+warn_return_any = true
+warn_unused_ignores = true
+disallow_untyped_defs = true
+disallow_incomplete_defs = true
+
+[[tool.mypy.overrides]]
+module = "tests.*"
+disallow_untyped_defs = false
+```
+
+Alternative: Use `pyright` for faster checking.
+
+```toml
+[tool.pyright]
+pythonVersion = "3.12"
+typeCheckingMode = "strict"
+```
+
+### Pattern 3: Naming Conventions
+
+Follow PEP 8 with emphasis on clarity over brevity.
+
+**Files and Modules:**
+
+```python
+# Good: Descriptive snake_case
+user_repository.py
+order_processing.py
+http_client.py
+
+# Avoid: Abbreviations
+usr_repo.py
+ord_proc.py
+http_cli.py
+```
+
+**Classes and Functions:**
+
+```python
+# Classes: PascalCase
+class UserRepository:
+    pass
+
+class HTTPClientFactory:  # Acronyms stay uppercase
+    pass
+
+# Functions and variables: snake_case
+def get_user_by_email(email: str) -> User | None:
+    retry_count = 3
+    max_connections = 100
+```
+
+**Constants:**
+
+```python
+# Module-level constants: SCREAMING_SNAKE_CASE
+MAX_RETRY_ATTEMPTS = 3
+DEFAULT_TIMEOUT_SECONDS = 30
+API_BASE_URL = "https://api.example.com"
+```
+
+### Pattern 4: Import Organization
+
+Group imports in a consistent order: standard library, third-party, local.
+
+```python
+# Standard library
+import os
+from collections.abc import Callable
+from typing import Any
+
+# Third-party packages
+import httpx
+from pydantic import BaseModel
+from sqlalchemy import Column
+
+# Local imports
+from myproject.models import User
+from myproject.services import UserService
+```
+
+Use absolute imports exclusively:
+
+```python
+# Preferred
+from myproject.utils import retry_decorator
+
+# Avoid relative imports
+from ..utils import retry_decorator
+```
+
+## Advanced Patterns
+
+### Pattern 5: Google-Style Docstrings
+
+Write docstrings for all public classes, methods, and functions.
+
+**Simple Function:**
+
+```python
+def get_user(user_id: str) -> User:
+    """Retrieve a user by their unique identifier."""
+    ...
+```
+
+**Complex Function:**
+
+```python
+def process_batch(
+    items: list[Item],
+    max_workers: int = 4,
+    on_progress: Callable[[int, int], None] | None = None,
+) -> BatchResult:
+    """Process items concurrently using a worker pool.
+
+    Processes each item in the batch using the configured number of
+    workers. Progress can be monitored via the optional callback.
+
+    Args:
+        items: The items to process. Must not be empty.
+        max_workers: Maximum concurrent workers. Defaults to 4.
+        on_progress: Optional callback receiving (completed, total) counts.
+
+    Returns:
+        BatchResult containing succeeded items and any failures with
+        their associated exceptions.
+
+    Raises:
+        ValueError: If items is empty.
+        ProcessingError: If the batch cannot be processed.
+
+    Example:
+        >>> result = process_batch(items, max_workers=8)
+        >>> print(f"Processed {len(result.succeeded)} items")
+    """
+    ...
+```
+
+**Class Docstring:**
+
+```python
+class UserService:
+    """Service for managing user operations.
+
+    Provides methods for creating, retrieving, updating, and
+    deleting users with proper validation and error handling.
+
+    Attributes:
+        repository: The data access layer for user persistence.
+        logger: Logger instance for operation tracking.
+
+    Example:
+        >>> service = UserService(repository, logger)
+        >>> user = service.create_user(CreateUserInput(...))
+    """
+
+    def __init__(self, repository: UserRepository, logger: Logger) -> None:
+        """Initialize the user service.
+
+        Args:
+            repository: Data access layer for users.
+            logger: Logger for tracking operations.
+        """
+        self.repository = repository
+        self.logger = logger
+```
+
+### Pattern 6: Line Length and Formatting
+
+Set line length to 120 characters for modern displays while maintaining readability.
+
+```python
+# Good: Readable line breaks
+def create_user(
+    email: str,
+    name: str,
+    role: UserRole = UserRole.MEMBER,
+    notify: bool = True,
+) -> User:
+    ...
+
+# Good: Chain method calls clearly
+result = (
+    db.query(User)
+    .filter(User.active == True)
+    .order_by(User.created_at.desc())
+    .limit(10)
+    .all()
+)
+
+# Good: Format long strings
+error_message = (
+    f"Failed to process user {user_id}: "
+    f"received status {response.status_code} "
+    f"with body {response.text[:100]}"
+)
+```
+
+### Pattern 7: Project Documentation
+
+**README Structure:**
+
+```markdown
+# Project Name
+
+Brief description of what the project does.
+
+## Installation
+
+\`\`\`bash
+pip install myproject
+\`\`\`
+
+## Quick Start
+
+\`\`\`python
+from myproject import Client
+
+client = Client(api_key="...")
+result = client.process(data)
+\`\`\`
+
+## Configuration
+
+Document environment variables and configuration options.
+
+## Development
+
+\`\`\`bash
+pip install -e ".[dev]"
+pytest
+\`\`\`
+```
+
+**CHANGELOG Format (Keep a Changelog):**
+
+```markdown
+# Changelog
+
+## [Unreleased]
+
+### Added
+- New feature X
+
+### Changed
+- Modified behavior of Y
+
+### Fixed
+- Bug in Z
+```
+
+## Best Practices Summary
+
+1. **Use ruff** - Single tool for linting and formatting
+2. **Enable strict mypy** - Catch type errors before runtime
+3. **120 character lines** - Modern standard for readability
+4. **Descriptive names** - Clarity over brevity
+5. **Absolute imports** - More maintainable than relative
+6. **Google-style docstrings** - Consistent, readable documentation
+7. **Document public APIs** - Every public function needs a docstring
+8. **Keep docs updated** - Treat documentation as code
+9. **Automate in CI** - Run linters on every commit
+10. **Target Python 3.10+** - For new projects, Python 3.12+ is recommended for modern language features
diff --git a/plugins/python-development/skills/python-configuration/SKILL.md b/plugins/python-development/skills/python-configuration/SKILL.md
new file mode 100644
index 0000000..3dd049f
--- /dev/null
+++ b/plugins/python-development/skills/python-configuration/SKILL.md
@@ -0,0 +1,368 @@
+---
+name: python-configuration
+description: Python configuration management via environment variables and typed settings. Use when externalizing config, setting up pydantic-settings, managing secrets, or implementing environment-specific behavior.
+---
+
+# Python Configuration Management
+
+Externalize configuration from code using environment variables and typed settings. Well-managed configuration enables the same code to run in any environment without modification.
+
+## When to Use This Skill
+
+- Setting up a new project's configuration system
+- Migrating from hardcoded values to environment variables
+- Implementing pydantic-settings for typed configuration
+- Managing secrets and sensitive values
+- Creating environment-specific settings (dev/staging/prod)
+- Validating configuration at application startup
+
+## Core Concepts
+
+### 1. Externalized Configuration
+
+All environment-specific values (URLs, secrets, feature flags) come from environment variables, not code.
+
+### 2. Typed Settings
+
+Parse and validate configuration into typed objects at startup, not scattered throughout code.
+
+### 3. Fail Fast
+
+Validate all required configuration at application boot. Missing config should crash immediately with a clear message.
+
+### 4. Sensible Defaults
+
+Provide reasonable defaults for local development while requiring explicit values for sensitive settings.
+
+## Quick Start
+
+```python
+from pydantic_settings import BaseSettings
+from pydantic import Field
+
+class Settings(BaseSettings):
+    database_url: str = Field(alias="DATABASE_URL")
+    api_key: str = Field(alias="API_KEY")
+    debug: bool = Field(default=False, alias="DEBUG")
+
+settings = Settings()  # Loads from environment
+```
+
+## Fundamental Patterns
+
+### Pattern 1: Typed Settings with Pydantic
+
+Create a central settings class that loads and validates all configuration.
+
+```python
+from pydantic_settings import BaseSettings
+from pydantic import Field, PostgresDsn, ValidationError
+import sys
+
+class Settings(BaseSettings):
+    """Application configuration loaded from environment variables."""
+
+    # Database
+    db_host: str = Field(alias="DB_HOST")
+    db_port: int = Field(default=5432, alias="DB_PORT")
+    db_name: str = Field(alias="DB_NAME")
+    db_user: str = Field(alias="DB_USER")
+    db_password: str = Field(alias="DB_PASSWORD")
+
+    # Redis
+    redis_url: str = Field(default="redis://localhost:6379", alias="REDIS_URL")
+
+    # API Keys
+    api_secret_key: str = Field(alias="API_SECRET_KEY")
+
+    # Feature flags
+    enable_new_feature: bool = Field(default=False, alias="ENABLE_NEW_FEATURE")
+
+    model_config = {
+        "env_file": ".env",
+        "env_file_encoding": "utf-8",
+    }
+
+# Create singleton instance at module load
+try:
+    settings = Settings()
+except ValidationError as e:
+    print(f"Configuration error:\n{e}")
+    sys.exit(1)
+```
+
+Import `settings` throughout your application:
+
+```python
+from myapp.config import settings
+
+def get_database_connection():
+    return connect(
+        host=settings.db_host,
+        port=settings.db_port,
+        database=settings.db_name,
+    )
+```
+
+### Pattern 2: Fail Fast on Missing Configuration
+
+Required settings should crash the application immediately with a clear error.
+
+```python
+from pydantic_settings import BaseSettings
+from pydantic import Field, ValidationError
+import sys
+
+class Settings(BaseSettings):
+    # Required - no default means it must be set
+    api_key: str = Field(alias="API_KEY")
+    database_url: str = Field(alias="DATABASE_URL")
+
+    # Optional with defaults
+    log_level: str = Field(default="INFO", alias="LOG_LEVEL")
+
+try:
+    settings = Settings()
+except ValidationError as e:
+    print("=" * 60)
+    print("CONFIGURATION ERROR")
+    print("=" * 60)
+    for error in e.errors():
+        field = error["loc"][0]
+        print(f"  - {field}: {error['msg']}")
+    print("\nPlease set the required environment variables.")
+    sys.exit(1)
+```
+
+A clear error at startup is better than a cryptic `None` failure mid-request.
+
+### Pattern 3: Local Development Defaults
+
+Provide sensible defaults for local development while requiring explicit values for secrets.
+
+```python
+class Settings(BaseSettings):
+    # Has local default, but prod will override
+    db_host: str = Field(default="localhost", alias="DB_HOST")
+    db_port: int = Field(default=5432, alias="DB_PORT")
+
+    # Always required - no default for secrets
+    db_password: str = Field(alias="DB_PASSWORD")
+    api_secret_key: str = Field(alias="API_SECRET_KEY")
+
+    # Development convenience
+    debug: bool = Field(default=False, alias="DEBUG")
+
+    model_config = {"env_file": ".env"}
+```
+
+Create a `.env` file for local development (never commit this):
+
+```bash
+# .env (add to .gitignore)
+DB_PASSWORD=local_dev_password
+API_SECRET_KEY=dev-secret-key
+DEBUG=true
+```
+
+### Pattern 4: Namespaced Environment Variables
+
+Prefix related variables for clarity and easy debugging.
+
+```bash
+# Database configuration
+DB_HOST=localhost
+DB_PORT=5432
+DB_NAME=myapp
+DB_USER=admin
+DB_PASSWORD=secret
+
+# Redis configuration
+REDIS_URL=redis://localhost:6379
+REDIS_MAX_CONNECTIONS=10
+
+# Authentication
+AUTH_SECRET_KEY=your-secret-key
+AUTH_TOKEN_EXPIRY_SECONDS=3600
+AUTH_ALGORITHM=HS256
+
+# Feature flags
+FEATURE_NEW_CHECKOUT=true
+FEATURE_BETA_UI=false
+```
+
+Makes `env | grep DB_` useful for debugging.
+
+## Advanced Patterns
+
+### Pattern 5: Type Coercion
+
+Pydantic handles common conversions automatically.
+
+```python
+from pydantic_settings import BaseSettings
+from pydantic import Field, field_validator
+
+class Settings(BaseSettings):
+    # Automatically converts "true", "1", "yes" to True
+    debug: bool = False
+
+    # Automatically converts string to int
+    max_connections: int = 100
+
+    # Parse comma-separated string to list
+    allowed_hosts: list[str] = Field(default_factory=list)
+
+    @field_validator("allowed_hosts", mode="before")
+    @classmethod
+    def parse_allowed_hosts(cls, v: str | list[str]) -> list[str]:
+        if isinstance(v, str):
+            return [host.strip() for host in v.split(",") if host.strip()]
+        return v
+```
+
+Usage:
+
+```bash
+ALLOWED_HOSTS=example.com,api.example.com,localhost
+MAX_CONNECTIONS=50
+DEBUG=true
+```
+
+### Pattern 6: Environment-Specific Configuration
+
+Use an environment enum to switch behavior.
+
+```python
+from enum import Enum
+from pydantic_settings import BaseSettings
+from pydantic import Field, computed_field
+
+class Environment(str, Enum):
+    LOCAL = "local"
+    STAGING = "staging"
+    PRODUCTION = "production"
+
+class Settings(BaseSettings):
+    environment: Environment = Field(
+        default=Environment.LOCAL,
+        alias="ENVIRONMENT",
+    )
+
+    # Settings that vary by environment
+    log_level: str = Field(default="DEBUG", alias="LOG_LEVEL")
+
+    @computed_field
+    @property
+    def is_production(self) -> bool:
+        return self.environment == Environment.PRODUCTION
+
+    @computed_field
+    @property
+    def is_local(self) -> bool:
+        return self.environment == Environment.LOCAL
+
+# Usage
+if settings.is_production:
+    configure_production_logging()
+else:
+    configure_debug_logging()
+```
+
+### Pattern 7: Nested Configuration Groups
+
+Organize related settings into nested models.
+
+```python
+from pydantic import BaseModel
+from pydantic_settings import BaseSettings
+
+class DatabaseSettings(BaseModel):
+    host: str = "localhost"
+    port: int = 5432
+    name: str
+    user: str
+    password: str
+
+class RedisSettings(BaseModel):
+    url: str = "redis://localhost:6379"
+    max_connections: int = 10
+
+class Settings(BaseSettings):
+    database: DatabaseSettings
+    redis: RedisSettings
+    debug: bool = False
+
+    model_config = {
+        "env_nested_delimiter": "__",
+        "env_file": ".env",
+    }
+```
+
+Environment variables use double underscore for nesting:
+
+```bash
+DATABASE__HOST=db.example.com
+DATABASE__PORT=5432
+DATABASE__NAME=myapp
+DATABASE__USER=admin
+DATABASE__PASSWORD=secret
+REDIS__URL=redis://redis.example.com:6379
+```
+
+### Pattern 8: Secrets from Files
+
+For container environments, read secrets from mounted files.
+
+```python
+from pydantic_settings import BaseSettings
+from pydantic import Field
+from pathlib import Path
+
+class Settings(BaseSettings):
+    # Read from environment variable or file
+    db_password: str = Field(alias="DB_PASSWORD")
+
+    model_config = {
+        "secrets_dir": "/run/secrets",  # Docker secrets location
+    }
+```
+
+Pydantic will look for `/run/secrets/db_password` if the env var isn't set.
+
+### Pattern 9: Configuration Validation
+
+Add custom validation for complex requirements.
+
+```python
+from pydantic_settings import BaseSettings
+from pydantic import Field, model_validator
+
+class Settings(BaseSettings):
+    db_host: str = Field(alias="DB_HOST")
+    db_port: int = Field(alias="DB_PORT")
+    read_replica_host: str | None = Field(default=None, alias="READ_REPLICA_HOST")
+    read_replica_port: int = Field(default=5432, alias="READ_REPLICA_PORT")
+
+    @model_validator(mode="after")
+    def validate_replica_settings(self):
+        if self.read_replica_host and self.read_replica_port == self.db_port:
+            if self.read_replica_host == self.db_host:
+                raise ValueError(
+                    "Read replica cannot be the same as primary database"
+                )
+        return self
+```
+
+## Best Practices Summary
+
+1. **Never hardcode config** - All environment-specific values from env vars
+2. **Use typed settings** - Pydantic-settings with validation
+3. **Fail fast** - Crash on missing required config at startup
+4. **Provide dev defaults** - Make local development easy
+5. **Never commit secrets** - Use `.env` files (gitignored) or secret managers
+6. **Namespace variables** - `DB_HOST`, `REDIS_URL` for clarity
+7. **Import settings singleton** - Don't call `os.getenv()` throughout code
+8. **Document all variables** - README should list required env vars
+9. **Validate early** - Check config correctness at boot time
+10. **Use secrets_dir** - Support mounted secrets in containers
diff --git a/plugins/python-development/skills/python-design-patterns/SKILL.md b/plugins/python-development/skills/python-design-patterns/SKILL.md
new file mode 100644
index 0000000..22603b6
--- /dev/null
+++ b/plugins/python-development/skills/python-design-patterns/SKILL.md
@@ -0,0 +1,411 @@
+---
+name: python-design-patterns
+description: Python design patterns including KISS, Separation of Concerns, Single Responsibility, and composition over inheritance. Use when making architecture decisions, refactoring code structure, or evaluating when abstractions are appropriate.
+---
+
+# Python Design Patterns
+
+Write maintainable Python code using fundamental design principles. These patterns help you build systems that are easy to understand, test, and modify.
+
+## When to Use This Skill
+
+- Designing new components or services
+- Refactoring complex or tangled code
+- Deciding whether to create an abstraction
+- Choosing between inheritance and composition
+- Evaluating code complexity and coupling
+- Planning modular architectures
+
+## Core Concepts
+
+### 1. KISS (Keep It Simple)
+
+Choose the simplest solution that works. Complexity must be justified by concrete requirements.
+
+### 2. Single Responsibility (SRP)
+
+Each unit should have one reason to change. Separate concerns into focused components.
+
+### 3. Composition Over Inheritance
+
+Build behavior by combining objects, not extending classes.
+
+### 4. Rule of Three
+
+Wait until you have three instances before abstracting. Duplication is often better than premature abstraction.
+
+## Quick Start
+
+```python
+# Simple beats clever
+# Instead of a factory/registry pattern:
+FORMATTERS = {"json": JsonFormatter, "csv": CsvFormatter}
+
+def get_formatter(name: str) -> Formatter:
+    return FORMATTERS[name]()
+```
+
+## Fundamental Patterns
+
+### Pattern 1: KISS - Keep It Simple
+
+Before adding complexity, ask: does a simpler solution work?
+
+```python
+# Over-engineered: Factory with registration
+class OutputFormatterFactory:
+    _formatters: dict[str, type[Formatter]] = {}
+
+    @classmethod
+    def register(cls, name: str):
+        def decorator(formatter_cls):
+            cls._formatters[name] = formatter_cls
+            return formatter_cls
+        return decorator
+
+    @classmethod
+    def create(cls, name: str) -> Formatter:
+        return cls._formatters[name]()
+
+@OutputFormatterFactory.register("json")
+class JsonFormatter(Formatter):
+    ...
+
+# Simple: Just use a dictionary
+FORMATTERS = {
+    "json": JsonFormatter,
+    "csv": CsvFormatter,
+    "xml": XmlFormatter,
+}
+
+def get_formatter(name: str) -> Formatter:
+    """Get formatter by name."""
+    if name not in FORMATTERS:
+        raise ValueError(f"Unknown format: {name}")
+    return FORMATTERS[name]()
+```
+
+The factory pattern adds code without adding value here. Save patterns for when they solve real problems.
+
+### Pattern 2: Single Responsibility Principle
+
+Each class or function should have one reason to change.
+
+```python
+# BAD: Handler does everything
+class UserHandler:
+    async def create_user(self, request: Request) -> Response:
+        # HTTP parsing
+        data = await request.json()
+
+        # Validation
+        if not data.get("email"):
+            return Response({"error": "email required"}, status=400)
+
+        # Database access
+        user = await db.execute(
+            "INSERT INTO users (email, name) VALUES ($1, $2) RETURNING *",
+            data["email"], data["name"]
+        )
+
+        # Response formatting
+        return Response({"id": user.id, "email": user.email}, status=201)
+
+# GOOD: Separated concerns
+class UserService:
+    """Business logic only."""
+
+    def __init__(self, repo: UserRepository) -> None:
+        self._repo = repo
+
+    async def create_user(self, data: CreateUserInput) -> User:
+        # Only business rules here
+        user = User(email=data.email, name=data.name)
+        return await self._repo.save(user)
+
+class UserHandler:
+    """HTTP concerns only."""
+
+    def __init__(self, service: UserService) -> None:
+        self._service = service
+
+    async def create_user(self, request: Request) -> Response:
+        data = CreateUserInput(**(await request.json()))
+        user = await self._service.create_user(data)
+        return Response(user.to_dict(), status=201)
+```
+
+Now HTTP changes don't affect business logic, and vice versa.
+
+### Pattern 3: Separation of Concerns
+
+Organize code into distinct layers with clear responsibilities.
+
+```
+┌─────────────────────────────────────────────────────┐
+│  API Layer (handlers)                                │
+│  - Parse requests                                    │
+│  - Call services                                     │
+│  - Format responses                                  │
+└─────────────────────────────────────────────────────┘
+                        │
+                        ▼
+┌─────────────────────────────────────────────────────┐
+│  Service Layer (business logic)                      │
+│  - Domain rules and validation                       │
+│  - Orchestrate operations                            │
+│  - Pure functions where possible                     │
+└─────────────────────────────────────────────────────┘
+                        │
+                        ▼
+┌─────────────────────────────────────────────────────┐
+│  Repository Layer (data access)                      │
+│  - SQL queries                                       │
+│  - External API calls                                │
+│  - Cache operations                                  │
+└─────────────────────────────────────────────────────┘
+```
+
+Each layer depends only on layers below it:
+
+```python
+# Repository: Data access
+class UserRepository:
+    async def get_by_id(self, user_id: str) -> User | None:
+        row = await self._db.fetchrow(
+            "SELECT * FROM users WHERE id = $1", user_id
+        )
+        return User(**row) if row else None
+
+# Service: Business logic
+class UserService:
+    def __init__(self, repo: UserRepository) -> None:
+        self._repo = repo
+
+    async def get_user(self, user_id: str) -> User:
+        user = await self._repo.get_by_id(user_id)
+        if user is None:
+            raise UserNotFoundError(user_id)
+        return user
+
+# Handler: HTTP concerns
+@app.get("/users/{user_id}")
+async def get_user(user_id: str) -> UserResponse:
+    user = await user_service.get_user(user_id)
+    return UserResponse.from_user(user)
+```
+
+### Pattern 4: Composition Over Inheritance
+
+Build behavior by combining objects rather than inheriting.
+
+```python
+# Inheritance: Rigid and hard to test
+class EmailNotificationService(NotificationService):
+    def __init__(self):
+        super().__init__()
+        self._smtp = SmtpClient()  # Hard to mock
+
+    def notify(self, user: User, message: str) -> None:
+        self._smtp.send(user.email, message)
+
+# Composition: Flexible and testable
+class NotificationService:
+    """Send notifications via multiple channels."""
+
+    def __init__(
+        self,
+        email_sender: EmailSender,
+        sms_sender: SmsSender | None = None,
+        push_sender: PushSender | None = None,
+    ) -> None:
+        self._email = email_sender
+        self._sms = sms_sender
+        self._push = push_sender
+
+    async def notify(
+        self,
+        user: User,
+        message: str,
+        channels: set[str] | None = None,
+    ) -> None:
+        channels = channels or {"email"}
+
+        if "email" in channels:
+            await self._email.send(user.email, message)
+
+        if "sms" in channels and self._sms and user.phone:
+            await self._sms.send(user.phone, message)
+
+        if "push" in channels and self._push and user.device_token:
+            await self._push.send(user.device_token, message)
+
+# Easy to test with fakes
+service = NotificationService(
+    email_sender=FakeEmailSender(),
+    sms_sender=FakeSmsSender(),
+)
+```
+
+## Advanced Patterns
+
+### Pattern 5: Rule of Three
+
+Wait until you have three instances before abstracting.
+
+```python
+# Two similar functions? Don't abstract yet
+def process_orders(orders: list[Order]) -> list[Result]:
+    results = []
+    for order in orders:
+        validated = validate_order(order)
+        result = process_validated_order(validated)
+        results.append(result)
+    return results
+
+def process_returns(returns: list[Return]) -> list[Result]:
+    results = []
+    for ret in returns:
+        validated = validate_return(ret)
+        result = process_validated_return(validated)
+        results.append(result)
+    return results
+
+# These look similar, but wait! Are they actually the same?
+# Different validation, different processing, different errors...
+# Duplication is often better than the wrong abstraction
+
+# Only after a third case, consider if there's a real pattern
+# But even then, sometimes explicit is better than abstract
+```
+
+### Pattern 6: Function Size Guidelines
+
+Keep functions focused. Extract when a function:
+
+- Exceeds 20-50 lines (varies by complexity)
+- Serves multiple distinct purposes
+- Has deeply nested logic (3+ levels)
+
+```python
+# Too long, multiple concerns mixed
+def process_order(order: Order) -> Result:
+    # 50 lines of validation...
+    # 30 lines of inventory check...
+    # 40 lines of payment processing...
+    # 20 lines of notification...
+    pass
+
+# Better: Composed from focused functions
+def process_order(order: Order) -> Result:
+    """Process a customer order through the complete workflow."""
+    validate_order(order)
+    reserve_inventory(order)
+    payment_result = charge_payment(order)
+    send_confirmation(order, payment_result)
+    return Result(success=True, order_id=order.id)
+```
+
+### Pattern 7: Dependency Injection
+
+Pass dependencies through constructors for testability.
+
+```python
+from typing import Protocol
+
+class Logger(Protocol):
+    def info(self, msg: str, **kwargs) -> None: ...
+    def error(self, msg: str, **kwargs) -> None: ...
+
+class Cache(Protocol):
+    async def get(self, key: str) -> str | None: ...
+    async def set(self, key: str, value: str, ttl: int) -> None: ...
+
+class UserService:
+    """Service with injected dependencies."""
+
+    def __init__(
+        self,
+        repository: UserRepository,
+        cache: Cache,
+        logger: Logger,
+    ) -> None:
+        self._repo = repository
+        self._cache = cache
+        self._logger = logger
+
+    async def get_user(self, user_id: str) -> User:
+        # Check cache first
+        cached = await self._cache.get(f"user:{user_id}")
+        if cached:
+            self._logger.info("Cache hit", user_id=user_id)
+            return User.from_json(cached)
+
+        # Fetch from database
+        user = await self._repo.get_by_id(user_id)
+        if user:
+            await self._cache.set(f"user:{user_id}", user.to_json(), ttl=300)
+
+        return user
+
+# Production
+service = UserService(
+    repository=PostgresUserRepository(db),
+    cache=RedisCache(redis),
+    logger=StructlogLogger(),
+)
+
+# Testing
+service = UserService(
+    repository=InMemoryUserRepository(),
+    cache=FakeCache(),
+    logger=NullLogger(),
+)
+```
+
+### Pattern 8: Avoiding Common Anti-Patterns
+
+**Don't expose internal types:**
+
+```python
+# BAD: Leaking ORM model to API
+@app.get("/users/{id}")
+def get_user(id: str) -> UserModel:  # SQLAlchemy model
+    return db.query(UserModel).get(id)
+
+# GOOD: Use response schemas
+@app.get("/users/{id}")
+def get_user(id: str) -> UserResponse:
+    user = db.query(UserModel).get(id)
+    return UserResponse.from_orm(user)
+```
+
+**Don't mix I/O with business logic:**
+
+```python
+# BAD: SQL embedded in business logic
+def calculate_discount(user_id: str) -> float:
+    user = db.query("SELECT * FROM users WHERE id = ?", user_id)
+    orders = db.query("SELECT * FROM orders WHERE user_id = ?", user_id)
+    # Business logic mixed with data access
+
+# GOOD: Repository pattern
+def calculate_discount(user: User, order_history: list[Order]) -> float:
+    # Pure business logic, easily testable
+    if len(order_history) > 10:
+        return 0.15
+    return 0.0
+```
+
+## Best Practices Summary
+
+1. **Keep it simple** - Choose the simplest solution that works
+2. **Single responsibility** - Each unit has one reason to change
+3. **Separate concerns** - Distinct layers with clear purposes
+4. **Compose, don't inherit** - Combine objects for flexibility
+5. **Rule of three** - Wait before abstracting
+6. **Keep functions small** - 20-50 lines (varies by complexity), one purpose
+7. **Inject dependencies** - Constructor injection for testability
+8. **Delete before abstracting** - Remove dead code, then consider patterns
+9. **Test each layer** - Isolated tests for each concern
+10. **Explicit over clever** - Readable code beats elegant code
diff --git a/plugins/python-development/skills/python-error-handling/SKILL.md b/plugins/python-development/skills/python-error-handling/SKILL.md
new file mode 100644
index 0000000..aa6d97c
--- /dev/null
+++ b/plugins/python-development/skills/python-error-handling/SKILL.md
@@ -0,0 +1,359 @@
+---
+name: python-error-handling
+description: Python error handling patterns including input validation, exception hierarchies, and partial failure handling. Use when implementing validation logic, designing exception strategies, handling batch processing failures, or building robust APIs.
+---
+
+# Python Error Handling
+
+Build robust Python applications with proper input validation, meaningful exceptions, and graceful failure handling. Good error handling makes debugging easier and systems more reliable.
+
+## When to Use This Skill
+
+- Validating user input and API parameters
+- Designing exception hierarchies for applications
+- Handling partial failures in batch operations
+- Converting external data to domain types
+- Building user-friendly error messages
+- Implementing fail-fast validation patterns
+
+## Core Concepts
+
+### 1. Fail Fast
+
+Validate inputs early, before expensive operations. Report all validation errors at once when possible.
+
+### 2. Meaningful Exceptions
+
+Use appropriate exception types with context. Messages should explain what failed, why, and how to fix it.
+
+### 3. Partial Failures
+
+In batch operations, don't let one failure abort everything. Track successes and failures separately.
+
+### 4. Preserve Context
+
+Chain exceptions to maintain the full error trail for debugging.
+
+## Quick Start
+
+```python
+def fetch_page(url: str, page_size: int) -> Page:
+    if not url:
+        raise ValueError("'url' is required")
+    if not 1 <= page_size <= 100:
+        raise ValueError(f"'page_size' must be 1-100, got {page_size}")
+    # Now safe to proceed...
+```
+
+## Fundamental Patterns
+
+### Pattern 1: Early Input Validation
+
+Validate all inputs at API boundaries before any processing begins.
+
+```python
+def process_order(
+    order_id: str,
+    quantity: int,
+    discount_percent: float,
+) -> OrderResult:
+    """Process an order with validation."""
+    # Validate required fields
+    if not order_id:
+        raise ValueError("'order_id' is required")
+
+    # Validate ranges
+    if quantity <= 0:
+        raise ValueError(f"'quantity' must be positive, got {quantity}")
+
+    if not 0 <= discount_percent <= 100:
+        raise ValueError(
+            f"'discount_percent' must be 0-100, got {discount_percent}"
+        )
+
+    # Validation passed, proceed with processing
+    return _process_validated_order(order_id, quantity, discount_percent)
+```
+
+### Pattern 2: Convert to Domain Types Early
+
+Parse strings and external data into typed domain objects at system boundaries.
+
+```python
+from enum import Enum
+
+class OutputFormat(Enum):
+    JSON = "json"
+    CSV = "csv"
+    PARQUET = "parquet"
+
+def parse_output_format(value: str) -> OutputFormat:
+    """Parse string to OutputFormat enum.
+
+    Args:
+        value: Format string from user input.
+
+    Returns:
+        Validated OutputFormat enum member.
+
+    Raises:
+        ValueError: If format is not recognized.
+    """
+    try:
+        return OutputFormat(value.lower())
+    except ValueError:
+        valid_formats = [f.value for f in OutputFormat]
+        raise ValueError(
+            f"Invalid format '{value}'. "
+            f"Valid options: {', '.join(valid_formats)}"
+        )
+
+# Usage at API boundary
+def export_data(data: list[dict], format_str: str) -> bytes:
+    output_format = parse_output_format(format_str)  # Fail fast
+    # Rest of function uses typed OutputFormat
+    ...
+```
+
+### Pattern 3: Pydantic for Complex Validation
+
+Use Pydantic models for structured input validation with automatic error messages.
+
+```python
+from pydantic import BaseModel, Field, field_validator
+
+class CreateUserInput(BaseModel):
+    """Input model for user creation."""
+
+    email: str = Field(..., min_length=5, max_length=255)
+    name: str = Field(..., min_length=1, max_length=100)
+    age: int = Field(ge=0, le=150)
+
+    @field_validator("email")
+    @classmethod
+    def validate_email_format(cls, v: str) -> str:
+        if "@" not in v or "." not in v.split("@")[-1]:
+            raise ValueError("Invalid email format")
+        return v.lower()
+
+    @field_validator("name")
+    @classmethod
+    def normalize_name(cls, v: str) -> str:
+        return v.strip().title()
+
+# Usage
+try:
+    user_input = CreateUserInput(
+        email="user@example.com",
+        name="john doe",
+        age=25,
+    )
+except ValidationError as e:
+    # Pydantic provides detailed error information
+    print(e.errors())
+```
+
+### Pattern 4: Map Errors to Standard Exceptions
+
+Use Python's built-in exception types appropriately, adding context as needed.
+
+| Failure Type | Exception | Example |
+|--------------|-----------|---------|
+| Invalid input | `ValueError` | Bad parameter values |
+| Wrong type | `TypeError` | Expected string, got int |
+| Missing item | `KeyError` | Dict key not found |
+| Operational failure | `RuntimeError` | Service unavailable |
+| Timeout | `TimeoutError` | Operation took too long |
+| File not found | `FileNotFoundError` | Path doesn't exist |
+| Permission denied | `PermissionError` | Access forbidden |
+
+```python
+# Good: Specific exception with context
+raise ValueError(f"'page_size' must be 1-100, got {page_size}")
+
+# Avoid: Generic exception, no context
+raise Exception("Invalid parameter")
+```
+
+## Advanced Patterns
+
+### Pattern 5: Custom Exceptions with Context
+
+Create domain-specific exceptions that carry structured information.
+
+```python
+class ApiError(Exception):
+    """Base exception for API errors."""
+
+    def __init__(
+        self,
+        message: str,
+        status_code: int,
+        response_body: str | None = None,
+    ) -> None:
+        self.status_code = status_code
+        self.response_body = response_body
+        super().__init__(message)
+
+class RateLimitError(ApiError):
+    """Raised when rate limit is exceeded."""
+
+    def __init__(self, retry_after: int) -> None:
+        self.retry_after = retry_after
+        super().__init__(
+            f"Rate limit exceeded. Retry after {retry_after}s",
+            status_code=429,
+        )
+
+# Usage
+def handle_response(response: Response) -> dict:
+    match response.status_code:
+        case 200:
+            return response.json()
+        case 401:
+            raise ApiError("Invalid credentials", 401)
+        case 404:
+            raise ApiError(f"Resource not found: {response.url}", 404)
+        case 429:
+            retry_after = int(response.headers.get("Retry-After", 60))
+            raise RateLimitError(retry_after)
+        case code if 400 <= code < 500:
+            raise ApiError(f"Client error: {response.text}", code)
+        case code if code >= 500:
+            raise ApiError(f"Server error: {response.text}", code)
+```
+
+### Pattern 6: Exception Chaining
+
+Preserve the original exception when re-raising to maintain the debug trail.
+
+```python
+import httpx
+
+class ServiceError(Exception):
+    """High-level service operation failed."""
+    pass
+
+def upload_file(path: str) -> str:
+    """Upload file and return URL."""
+    try:
+        with open(path, "rb") as f:
+            response = httpx.post("https://upload.example.com", files={"file": f})
+            response.raise_for_status()
+            return response.json()["url"]
+    except FileNotFoundError as e:
+        raise ServiceError(f"Upload failed: file not found at '{path}'") from e
+    except httpx.HTTPStatusError as e:
+        raise ServiceError(
+            f"Upload failed: server returned {e.response.status_code}"
+        ) from e
+    except httpx.RequestError as e:
+        raise ServiceError(f"Upload failed: network error") from e
+```
+
+### Pattern 7: Batch Processing with Partial Failures
+
+Never let one bad item abort an entire batch. Track results per item.
+
+```python
+from dataclasses import dataclass
+
+@dataclass
+class BatchResult[T]:
+    """Results from batch processing."""
+
+    succeeded: dict[int, T]  # index -> result
+    failed: dict[int, Exception]  # index -> error
+
+    @property
+    def success_count(self) -> int:
+        return len(self.succeeded)
+
+    @property
+    def failure_count(self) -> int:
+        return len(self.failed)
+
+    @property
+    def all_succeeded(self) -> bool:
+        return len(self.failed) == 0
+
+def process_batch(items: list[Item]) -> BatchResult[ProcessedItem]:
+    """Process items, capturing individual failures.
+
+    Args:
+        items: Items to process.
+
+    Returns:
+        BatchResult with succeeded and failed items by index.
+    """
+    succeeded: dict[int, ProcessedItem] = {}
+    failed: dict[int, Exception] = {}
+
+    for idx, item in enumerate(items):
+        try:
+            result = process_single_item(item)
+            succeeded[idx] = result
+        except Exception as e:
+            failed[idx] = e
+
+    return BatchResult(succeeded=succeeded, failed=failed)
+
+# Caller handles partial results
+result = process_batch(items)
+if not result.all_succeeded:
+    logger.warning(
+        f"Batch completed with {result.failure_count} failures",
+        failed_indices=list(result.failed.keys()),
+    )
+```
+
+### Pattern 8: Progress Reporting for Long Operations
+
+Provide visibility into batch progress without coupling business logic to UI.
+
+```python
+from collections.abc import Callable
+
+ProgressCallback = Callable[[int, int, str], None]  # current, total, status
+
+def process_large_batch(
+    items: list[Item],
+    on_progress: ProgressCallback | None = None,
+) -> BatchResult:
+    """Process batch with optional progress reporting.
+
+    Args:
+        items: Items to process.
+        on_progress: Optional callback receiving (current, total, status).
+    """
+    total = len(items)
+    succeeded = {}
+    failed = {}
+
+    for idx, item in enumerate(items):
+        if on_progress:
+            on_progress(idx, total, f"Processing {item.id}")
+
+        try:
+            succeeded[idx] = process_single_item(item)
+        except Exception as e:
+            failed[idx] = e
+
+    if on_progress:
+        on_progress(total, total, "Complete")
+
+    return BatchResult(succeeded=succeeded, failed=failed)
+```
+
+## Best Practices Summary
+
+1. **Validate early** - Check inputs before expensive operations
+2. **Use specific exceptions** - `ValueError`, `TypeError`, not generic `Exception`
+3. **Include context** - Messages should explain what, why, and how to fix
+4. **Convert types at boundaries** - Parse strings to enums/domain types early
+5. **Chain exceptions** - Use `raise ... from e` to preserve debug info
+6. **Handle partial failures** - Don't abort batches on single item errors
+7. **Use Pydantic** - For complex input validation with structured errors
+8. **Document failure modes** - Docstrings should list possible exceptions
+9. **Log with context** - Include IDs, counts, and other debugging info
+10. **Test error paths** - Verify exceptions are raised correctly
diff --git a/plugins/python-development/skills/python-observability/SKILL.md b/plugins/python-development/skills/python-observability/SKILL.md
new file mode 100644
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--- /dev/null
+++ b/plugins/python-development/skills/python-observability/SKILL.md
@@ -0,0 +1,400 @@
+---
+name: python-observability
+description: Python observability patterns including structured logging, metrics, and distributed tracing. Use when adding logging, implementing metrics collection, setting up tracing, or debugging production systems.
+---
+
+# Python Observability
+
+Instrument Python applications with structured logs, metrics, and traces. When something breaks in production, you need to answer "what, where, and why" without deploying new code.
+
+## When to Use This Skill
+
+- Adding structured logging to applications
+- Implementing metrics collection with Prometheus
+- Setting up distributed tracing across services
+- Propagating correlation IDs through request chains
+- Debugging production issues
+- Building observability dashboards
+
+## Core Concepts
+
+### 1. Structured Logging
+
+Emit logs as JSON with consistent fields for production environments. Machine-readable logs enable powerful queries and alerts. For local development, consider human-readable formats.
+
+### 2. The Four Golden Signals
+
+Track latency, traffic, errors, and saturation for every service boundary.
+
+### 3. Correlation IDs
+
+Thread a unique ID through all logs and spans for a single request, enabling end-to-end tracing.
+
+### 4. Bounded Cardinality
+
+Keep metric label values bounded. Unbounded labels (like user IDs) explode storage costs.
+
+## Quick Start
+
+```python
+import structlog
+
+structlog.configure(
+    processors=[
+        structlog.processors.TimeStamper(fmt="iso"),
+        structlog.processors.JSONRenderer(),
+    ],
+)
+
+logger = structlog.get_logger()
+logger.info("Request processed", user_id="123", duration_ms=45)
+```
+
+## Fundamental Patterns
+
+### Pattern 1: Structured Logging with Structlog
+
+Configure structlog for JSON output with consistent fields.
+
+```python
+import logging
+import structlog
+
+def configure_logging(log_level: str = "INFO") -> None:
+    """Configure structured logging for the application."""
+    structlog.configure(
+        processors=[
+            structlog.contextvars.merge_contextvars,
+            structlog.processors.add_log_level,
+            structlog.processors.TimeStamper(fmt="iso"),
+            structlog.processors.StackInfoRenderer(),
+            structlog.processors.format_exc_info,
+            structlog.processors.JSONRenderer(),
+        ],
+        wrapper_class=structlog.make_filtering_bound_logger(
+            getattr(logging, log_level.upper())
+        ),
+        context_class=dict,
+        logger_factory=structlog.PrintLoggerFactory(),
+        cache_logger_on_first_use=True,
+    )
+
+# Initialize at application startup
+configure_logging("INFO")
+logger = structlog.get_logger()
+```
+
+### Pattern 2: Consistent Log Fields
+
+Every log entry should include standard fields for filtering and correlation.
+
+```python
+import structlog
+from contextvars import ContextVar
+
+# Store correlation ID in context
+correlation_id: ContextVar[str] = ContextVar("correlation_id", default="")
+
+logger = structlog.get_logger()
+
+def process_request(request: Request) -> Response:
+    """Process request with structured logging."""
+    logger.info(
+        "Request received",
+        correlation_id=correlation_id.get(),
+        method=request.method,
+        path=request.path,
+        user_id=request.user_id,
+    )
+
+    try:
+        result = handle_request(request)
+        logger.info(
+            "Request completed",
+            correlation_id=correlation_id.get(),
+            status_code=200,
+            duration_ms=elapsed,
+        )
+        return result
+    except Exception as e:
+        logger.error(
+            "Request failed",
+            correlation_id=correlation_id.get(),
+            error_type=type(e).__name__,
+            error_message=str(e),
+        )
+        raise
+```
+
+### Pattern 3: Semantic Log Levels
+
+Use log levels consistently across the application.
+
+| Level | Purpose | Examples |
+|-------|---------|----------|
+| `DEBUG` | Development diagnostics | Variable values, internal state |
+| `INFO` | Request lifecycle, operations | Request start/end, job completion |
+| `WARNING` | Recoverable anomalies | Retry attempts, fallback used |
+| `ERROR` | Failures needing attention | Exceptions, service unavailable |
+
+```python
+# DEBUG: Detailed internal information
+logger.debug("Cache lookup", key=cache_key, hit=cache_hit)
+
+# INFO: Normal operational events
+logger.info("Order created", order_id=order.id, total=order.total)
+
+# WARNING: Abnormal but handled situations
+logger.warning(
+    "Rate limit approaching",
+    current_rate=950,
+    limit=1000,
+    reset_seconds=30,
+)
+
+# ERROR: Failures requiring investigation
+logger.error(
+    "Payment processing failed",
+    order_id=order.id,
+    error=str(e),
+    payment_provider="stripe",
+)
+```
+
+Never log expected behavior at `ERROR`. A user entering a wrong password is `INFO`, not `ERROR`.
+
+### Pattern 4: Correlation ID Propagation
+
+Generate a unique ID at ingress and thread it through all operations.
+
+```python
+from contextvars import ContextVar
+import uuid
+import structlog
+
+correlation_id: ContextVar[str] = ContextVar("correlation_id", default="")
+
+def set_correlation_id(cid: str | None = None) -> str:
+    """Set correlation ID for current context."""
+    cid = cid or str(uuid.uuid4())
+    correlation_id.set(cid)
+    structlog.contextvars.bind_contextvars(correlation_id=cid)
+    return cid
+
+# FastAPI middleware example
+from fastapi import Request
+
+async def correlation_middleware(request: Request, call_next):
+    """Middleware to set and propagate correlation ID."""
+    # Use incoming header or generate new
+    cid = request.headers.get("X-Correlation-ID") or str(uuid.uuid4())
+    set_correlation_id(cid)
+
+    response = await call_next(request)
+    response.headers["X-Correlation-ID"] = cid
+    return response
+```
+
+Propagate to outbound requests:
+
+```python
+import httpx
+
+async def call_downstream_service(endpoint: str, data: dict) -> dict:
+    """Call downstream service with correlation ID."""
+    async with httpx.AsyncClient() as client:
+        response = await client.post(
+            endpoint,
+            json=data,
+            headers={"X-Correlation-ID": correlation_id.get()},
+        )
+        return response.json()
+```
+
+## Advanced Patterns
+
+### Pattern 5: The Four Golden Signals with Prometheus
+
+Track these metrics for every service boundary:
+
+```python
+from prometheus_client import Counter, Histogram, Gauge
+
+# Latency: How long requests take
+REQUEST_LATENCY = Histogram(
+    "http_request_duration_seconds",
+    "Request latency in seconds",
+    ["method", "endpoint", "status"],
+    buckets=[0.01, 0.025, 0.05, 0.1, 0.25, 0.5, 1, 2.5, 5, 10],
+)
+
+# Traffic: Request rate
+REQUEST_COUNT = Counter(
+    "http_requests_total",
+    "Total HTTP requests",
+    ["method", "endpoint", "status"],
+)
+
+# Errors: Error rate
+ERROR_COUNT = Counter(
+    "http_errors_total",
+    "Total HTTP errors",
+    ["method", "endpoint", "error_type"],
+)
+
+# Saturation: Resource utilization
+DB_POOL_USAGE = Gauge(
+    "db_connection_pool_used",
+    "Number of database connections in use",
+)
+```
+
+Instrument your endpoints:
+
+```python
+import time
+from functools import wraps
+
+def track_request(func):
+    """Decorator to track request metrics."""
+    @wraps(func)
+    async def wrapper(request: Request, *args, **kwargs):
+        method = request.method
+        endpoint = request.url.path
+        start = time.perf_counter()
+
+        try:
+            response = await func(request, *args, **kwargs)
+            status = str(response.status_code)
+            return response
+        except Exception as e:
+            status = "500"
+            ERROR_COUNT.labels(
+                method=method,
+                endpoint=endpoint,
+                error_type=type(e).__name__,
+            ).inc()
+            raise
+        finally:
+            duration = time.perf_counter() - start
+            REQUEST_COUNT.labels(method=method, endpoint=endpoint, status=status).inc()
+            REQUEST_LATENCY.labels(method=method, endpoint=endpoint, status=status).observe(duration)
+
+    return wrapper
+```
+
+### Pattern 6: Bounded Cardinality
+
+Avoid labels with unbounded values to prevent metric explosion.
+
+```python
+# BAD: User ID has potentially millions of values
+REQUEST_COUNT.labels(method="GET", user_id=user.id)  # Don't do this!
+
+# GOOD: Bounded values only
+REQUEST_COUNT.labels(method="GET", endpoint="/users", status="200")
+
+# If you need per-user metrics, use a different approach:
+# - Log the user_id and query logs
+# - Use a separate analytics system
+# - Bucket users by type/tier
+REQUEST_COUNT.labels(
+    method="GET",
+    endpoint="/users",
+    user_tier="premium",  # Bounded set of values
+)
+```
+
+### Pattern 7: Timed Operations with Context Manager
+
+Create a reusable timing context manager for operations.
+
+```python
+from contextlib import contextmanager
+import time
+import structlog
+
+logger = structlog.get_logger()
+
+@contextmanager
+def timed_operation(name: str, **extra_fields):
+    """Context manager for timing and logging operations."""
+    start = time.perf_counter()
+    logger.debug("Operation started", operation=name, **extra_fields)
+
+    try:
+        yield
+    except Exception as e:
+        elapsed_ms = (time.perf_counter() - start) * 1000
+        logger.error(
+            "Operation failed",
+            operation=name,
+            duration_ms=round(elapsed_ms, 2),
+            error=str(e),
+            **extra_fields,
+        )
+        raise
+    else:
+        elapsed_ms = (time.perf_counter() - start) * 1000
+        logger.info(
+            "Operation completed",
+            operation=name,
+            duration_ms=round(elapsed_ms, 2),
+            **extra_fields,
+        )
+
+# Usage
+with timed_operation("fetch_user_orders", user_id=user.id):
+    orders = await order_repository.get_by_user(user.id)
+```
+
+### Pattern 8: OpenTelemetry Tracing
+
+Set up distributed tracing with OpenTelemetry.
+
+**Note:** OpenTelemetry is actively evolving. Check the [official Python documentation](https://opentelemetry.io/docs/languages/python/) for the latest API patterns and best practices.
+
+```python
+from opentelemetry import trace
+from opentelemetry.sdk.trace import TracerProvider
+from opentelemetry.sdk.trace.export import BatchSpanProcessor
+from opentelemetry.exporter.otlp.proto.grpc.trace_exporter import OTLPSpanExporter
+
+def configure_tracing(service_name: str, otlp_endpoint: str) -> None:
+    """Configure OpenTelemetry tracing."""
+    provider = TracerProvider()
+    processor = BatchSpanProcessor(OTLPSpanExporter(endpoint=otlp_endpoint))
+    provider.add_span_processor(processor)
+    trace.set_tracer_provider(provider)
+
+tracer = trace.get_tracer(__name__)
+
+async def process_order(order_id: str) -> Order:
+    """Process order with tracing."""
+    with tracer.start_as_current_span("process_order") as span:
+        span.set_attribute("order.id", order_id)
+
+        with tracer.start_as_current_span("validate_order"):
+            validate_order(order_id)
+
+        with tracer.start_as_current_span("charge_payment"):
+            charge_payment(order_id)
+
+        with tracer.start_as_current_span("send_confirmation"):
+            send_confirmation(order_id)
+
+        return order
+```
+
+## Best Practices Summary
+
+1. **Use structured logging** - JSON logs with consistent fields
+2. **Propagate correlation IDs** - Thread through all requests and logs
+3. **Track the four golden signals** - Latency, traffic, errors, saturation
+4. **Bound label cardinality** - Never use unbounded values as metric labels
+5. **Log at appropriate levels** - Don't cry wolf with ERROR
+6. **Include context** - User ID, request ID, operation name in logs
+7. **Use context managers** - Consistent timing and error handling
+8. **Separate concerns** - Observability code shouldn't pollute business logic
+9. **Test your observability** - Verify logs and metrics in integration tests
+10. **Set up alerts** - Metrics are useless without alerting
diff --git a/plugins/python-development/skills/python-project-structure/SKILL.md b/plugins/python-development/skills/python-project-structure/SKILL.md
new file mode 100644
index 0000000..504df63
--- /dev/null
+++ b/plugins/python-development/skills/python-project-structure/SKILL.md
@@ -0,0 +1,252 @@
+---
+name: python-project-structure
+description: Python project organization, module architecture, and public API design. Use when setting up new projects, organizing modules, defining public interfaces with __all__, or planning directory layouts.
+---
+
+# Python Project Structure & Module Architecture
+
+Design well-organized Python projects with clear module boundaries, explicit public interfaces, and maintainable directory structures. Good organization makes code discoverable and changes predictable.
+
+## When to Use This Skill
+
+- Starting a new Python project from scratch
+- Reorganizing an existing codebase for clarity
+- Defining module public APIs with `__all__`
+- Deciding between flat and nested directory structures
+- Determining test file placement strategies
+- Creating reusable library packages
+
+## Core Concepts
+
+### 1. Module Cohesion
+
+Group related code that changes together. A module should have a single, clear purpose.
+
+### 2. Explicit Interfaces
+
+Define what's public with `__all__`. Everything not listed is an internal implementation detail.
+
+### 3. Flat Hierarchies
+
+Prefer shallow directory structures. Add depth only for genuine sub-domains.
+
+### 4. Consistent Conventions
+
+Apply naming and organization patterns uniformly across the project.
+
+## Quick Start
+
+```
+myproject/
+├── src/
+│   └── myproject/
+│       ├── __init__.py
+│       ├── services/
+│       ├── models/
+│       └── api/
+├── tests/
+├── pyproject.toml
+└── README.md
+```
+
+## Fundamental Patterns
+
+### Pattern 1: One Concept Per File
+
+Each file should focus on a single concept or closely related set of functions. Consider splitting when a file:
+
+- Handles multiple unrelated responsibilities
+- Grows beyond 300-500 lines (varies by complexity)
+- Contains classes that change for different reasons
+
+```python
+# Good: Focused files
+# user_service.py - User business logic
+# user_repository.py - User data access
+# user_models.py - User data structures
+
+# Avoid: Kitchen sink files
+# user.py - Contains service, repository, models, utilities...
+```
+
+### Pattern 2: Explicit Public APIs with `__all__`
+
+Define the public interface for every module. Unlisted members are internal implementation details.
+
+```python
+# mypackage/services/__init__.py
+from .user_service import UserService
+from .order_service import OrderService
+from .exceptions import ServiceError, ValidationError
+
+__all__ = [
+    "UserService",
+    "OrderService",
+    "ServiceError",
+    "ValidationError",
+]
+
+# Internal helpers remain private by omission
+# from .internal_helpers import _validate_input  # Not exported
+```
+
+### Pattern 3: Flat Directory Structure
+
+Prefer minimal nesting. Deep hierarchies make imports verbose and navigation difficult.
+
+```
+# Preferred: Flat structure
+project/
+├── api/
+│   ├── routes.py
+│   └── middleware.py
+├── services/
+│   ├── user_service.py
+│   └── order_service.py
+├── models/
+│   ├── user.py
+│   └── order.py
+└── utils/
+    └── validation.py
+
+# Avoid: Deep nesting
+project/core/internal/services/impl/user/
+```
+
+Add sub-packages only when there's a genuine sub-domain requiring isolation.
+
+### Pattern 4: Test File Organization
+
+Choose one approach and apply it consistently throughout the project.
+
+**Option A: Colocated Tests**
+
+```
+src/
+├── user_service.py
+├── test_user_service.py
+├── order_service.py
+└── test_order_service.py
+```
+
+Benefits: Tests live next to the code they verify. Easy to see coverage gaps.
+
+**Option B: Parallel Test Directory**
+
+```
+src/
+├── services/
+│   ├── user_service.py
+│   └── order_service.py
+tests/
+├── services/
+│   ├── test_user_service.py
+│   └── test_order_service.py
+```
+
+Benefits: Clean separation between production and test code. Standard for larger projects.
+
+## Advanced Patterns
+
+### Pattern 5: Package Initialization
+
+Use `__init__.py` to provide a clean public interface for package consumers.
+
+```python
+# mypackage/__init__.py
+"""MyPackage - A library for doing useful things."""
+
+from .core import MainClass, HelperClass
+from .exceptions import PackageError, ConfigError
+from .config import Settings
+
+__all__ = [
+    "MainClass",
+    "HelperClass",
+    "PackageError",
+    "ConfigError",
+    "Settings",
+]
+
+__version__ = "1.0.0"
+```
+
+Consumers can then import directly from the package:
+
+```python
+from mypackage import MainClass, Settings
+```
+
+### Pattern 6: Layered Architecture
+
+Organize code by architectural layer for clear separation of concerns.
+
+```
+myapp/
+├── api/           # HTTP handlers, request/response
+│   ├── routes/
+│   └── middleware/
+├── services/      # Business logic
+├── repositories/  # Data access
+├── models/        # Domain entities
+├── schemas/       # API schemas (Pydantic)
+└── config/        # Configuration
+```
+
+Each layer should only depend on layers below it, never above.
+
+### Pattern 7: Domain-Driven Structure
+
+For complex applications, organize by business domain rather than technical layer.
+
+```
+ecommerce/
+├── users/
+│   ├── models.py
+│   ├── services.py
+│   ├── repository.py
+│   └── api.py
+├── orders/
+│   ├── models.py
+│   ├── services.py
+│   ├── repository.py
+│   └── api.py
+└── shared/
+    ├── database.py
+    └── exceptions.py
+```
+
+## File and Module Naming
+
+### Conventions
+
+- Use `snake_case` for all file and module names: `user_repository.py`
+- Avoid abbreviations that obscure meaning: `user_repository.py` not `usr_repo.py`
+- Match class names to file names: `UserService` in `user_service.py`
+
+### Import Style
+
+Use absolute imports for clarity and reliability:
+
+```python
+# Preferred: Absolute imports
+from myproject.services import UserService
+from myproject.models import User
+
+# Avoid: Relative imports
+from ..services import UserService
+from . import models
+```
+
+Relative imports can break when modules are moved or reorganized.
+
+## Best Practices Summary
+
+1. **Keep files focused** - One concept per file, consider splitting at 300-500 lines (varies by complexity)
+2. **Define `__all__` explicitly** - Make public interfaces clear
+3. **Prefer flat structures** - Add depth only for genuine sub-domains
+4. **Use absolute imports** - More reliable and clearer
+5. **Be consistent** - Apply patterns uniformly across the project
+6. **Match names to content** - File names should describe their purpose
+7. **Separate concerns** - Keep layers distinct and dependencies flowing one direction
+8. **Document your structure** - Include a README explaining the organization
diff --git a/plugins/python-development/skills/python-resilience/SKILL.md b/plugins/python-development/skills/python-resilience/SKILL.md
new file mode 100644
index 0000000..27c5111
--- /dev/null
+++ b/plugins/python-development/skills/python-resilience/SKILL.md
@@ -0,0 +1,376 @@
+---
+name: python-resilience
+description: Python resilience patterns including automatic retries, exponential backoff, timeouts, and fault-tolerant decorators. Use when adding retry logic, implementing timeouts, building fault-tolerant services, or handling transient failures.
+---
+
+# Python Resilience Patterns
+
+Build fault-tolerant Python applications that gracefully handle transient failures, network issues, and service outages. Resilience patterns keep systems running when dependencies are unreliable.
+
+## When to Use This Skill
+
+- Adding retry logic to external service calls
+- Implementing timeouts for network operations
+- Building fault-tolerant microservices
+- Handling rate limiting and backpressure
+- Creating infrastructure decorators
+- Designing circuit breakers
+
+## Core Concepts
+
+### 1. Transient vs Permanent Failures
+
+Retry transient errors (network timeouts, temporary service issues). Don't retry permanent errors (invalid credentials, bad requests).
+
+### 2. Exponential Backoff
+
+Increase wait time between retries to avoid overwhelming recovering services.
+
+### 3. Jitter
+
+Add randomness to backoff to prevent thundering herd when many clients retry simultaneously.
+
+### 4. Bounded Retries
+
+Cap both attempt count and total duration to prevent infinite retry loops.
+
+## Quick Start
+
+```python
+from tenacity import retry, stop_after_attempt, wait_exponential_jitter
+
+@retry(
+    stop=stop_after_attempt(3),
+    wait=wait_exponential_jitter(initial=1, max=10),
+)
+def call_external_service(request: dict) -> dict:
+    return httpx.post("https://api.example.com", json=request).json()
+```
+
+## Fundamental Patterns
+
+### Pattern 1: Basic Retry with Tenacity
+
+Use the `tenacity` library for production-grade retry logic. For simpler cases, consider built-in retry functionality or a lightweight custom implementation.
+
+```python
+from tenacity import (
+    retry,
+    stop_after_attempt,
+    stop_after_delay,
+    wait_exponential_jitter,
+    retry_if_exception_type,
+)
+
+TRANSIENT_ERRORS = (ConnectionError, TimeoutError, OSError)
+
+@retry(
+    retry=retry_if_exception_type(TRANSIENT_ERRORS),
+    stop=stop_after_attempt(5) | stop_after_delay(60),
+    wait=wait_exponential_jitter(initial=1, max=30),
+)
+def fetch_data(url: str) -> dict:
+    """Fetch data with automatic retry on transient failures."""
+    response = httpx.get(url, timeout=30)
+    response.raise_for_status()
+    return response.json()
+```
+
+### Pattern 2: Retry Only Appropriate Errors
+
+Whitelist specific transient exceptions. Never retry:
+
+- `ValueError`, `TypeError` - These are bugs, not transient issues
+- `AuthenticationError` - Invalid credentials won't become valid
+- HTTP 4xx errors (except 429) - Client errors are permanent
+
+```python
+from tenacity import retry, retry_if_exception_type
+import httpx
+
+# Define what's retryable
+RETRYABLE_EXCEPTIONS = (
+    ConnectionError,
+    TimeoutError,
+    httpx.ConnectTimeout,
+    httpx.ReadTimeout,
+)
+
+@retry(
+    retry=retry_if_exception_type(RETRYABLE_EXCEPTIONS),
+    stop=stop_after_attempt(3),
+    wait=wait_exponential_jitter(initial=1, max=10),
+)
+def resilient_api_call(endpoint: str) -> dict:
+    """Make API call with retry on network issues."""
+    return httpx.get(endpoint, timeout=10).json()
+```
+
+### Pattern 3: HTTP Status Code Retries
+
+Retry specific HTTP status codes that indicate transient issues.
+
+```python
+from tenacity import retry, retry_if_result, stop_after_attempt
+import httpx
+
+RETRY_STATUS_CODES = {429, 502, 503, 504}
+
+def should_retry_response(response: httpx.Response) -> bool:
+    """Check if response indicates a retryable error."""
+    return response.status_code in RETRY_STATUS_CODES
+
+@retry(
+    retry=retry_if_result(should_retry_response),
+    stop=stop_after_attempt(3),
+    wait=wait_exponential_jitter(initial=1, max=10),
+)
+def http_request(method: str, url: str, **kwargs) -> httpx.Response:
+    """Make HTTP request with retry on transient status codes."""
+    return httpx.request(method, url, timeout=30, **kwargs)
+```
+
+### Pattern 4: Combined Exception and Status Retry
+
+Handle both network exceptions and HTTP status codes.
+
+```python
+from tenacity import (
+    retry,
+    retry_if_exception_type,
+    retry_if_result,
+    stop_after_attempt,
+    wait_exponential_jitter,
+    before_sleep_log,
+)
+import logging
+import httpx
+
+logger = logging.getLogger(__name__)
+
+TRANSIENT_EXCEPTIONS = (
+    ConnectionError,
+    TimeoutError,
+    httpx.ConnectError,
+    httpx.ReadTimeout,
+)
+RETRY_STATUS_CODES = {429, 500, 502, 503, 504}
+
+def is_retryable_response(response: httpx.Response) -> bool:
+    return response.status_code in RETRY_STATUS_CODES
+
+@retry(
+    retry=(
+        retry_if_exception_type(TRANSIENT_EXCEPTIONS) |
+        retry_if_result(is_retryable_response)
+    ),
+    stop=stop_after_attempt(5),
+    wait=wait_exponential_jitter(initial=1, max=30),
+    before_sleep=before_sleep_log(logger, logging.WARNING),
+)
+def robust_http_call(
+    method: str,
+    url: str,
+    **kwargs,
+) -> httpx.Response:
+    """HTTP call with comprehensive retry handling."""
+    return httpx.request(method, url, timeout=30, **kwargs)
+```
+
+## Advanced Patterns
+
+### Pattern 5: Logging Retry Attempts
+
+Track retry behavior for debugging and alerting.
+
+```python
+from tenacity import retry, stop_after_attempt, wait_exponential
+import structlog
+
+logger = structlog.get_logger()
+
+def log_retry_attempt(retry_state):
+    """Log detailed retry information."""
+    exception = retry_state.outcome.exception()
+    logger.warning(
+        "Retrying operation",
+        attempt=retry_state.attempt_number,
+        exception_type=type(exception).__name__,
+        exception_message=str(exception),
+        next_wait_seconds=retry_state.next_action.sleep if retry_state.next_action else None,
+    )
+
+@retry(
+    stop=stop_after_attempt(3),
+    wait=wait_exponential(multiplier=1, max=10),
+    before_sleep=log_retry_attempt,
+)
+def call_with_logging(request: dict) -> dict:
+    """External call with retry logging."""
+    ...
+```
+
+### Pattern 6: Timeout Decorator
+
+Create reusable timeout decorators for consistent timeout handling.
+
+```python
+import asyncio
+from functools import wraps
+from typing import TypeVar, Callable
+
+T = TypeVar("T")
+
+def with_timeout(seconds: float):
+    """Decorator to add timeout to async functions."""
+    def decorator(func: Callable[..., T]) -> Callable[..., T]:
+        @wraps(func)
+        async def wrapper(*args, **kwargs) -> T:
+            return await asyncio.wait_for(
+                func(*args, **kwargs),
+                timeout=seconds,
+            )
+        return wrapper
+    return decorator
+
+@with_timeout(30)
+async def fetch_with_timeout(url: str) -> dict:
+    """Fetch URL with 30 second timeout."""
+    async with httpx.AsyncClient() as client:
+        response = await client.get(url)
+        return response.json()
+```
+
+### Pattern 7: Cross-Cutting Concerns via Decorators
+
+Stack decorators to separate infrastructure from business logic.
+
+```python
+from functools import wraps
+from typing import TypeVar, Callable
+import structlog
+
+logger = structlog.get_logger()
+T = TypeVar("T")
+
+def traced(name: str | None = None):
+    """Add tracing to function calls."""
+    def decorator(func: Callable[..., T]) -> Callable[..., T]:
+        span_name = name or func.__name__
+
+        @wraps(func)
+        async def wrapper(*args, **kwargs) -> T:
+            logger.info("Operation started", operation=span_name)
+            try:
+                result = await func(*args, **kwargs)
+                logger.info("Operation completed", operation=span_name)
+                return result
+            except Exception as e:
+                logger.error("Operation failed", operation=span_name, error=str(e))
+                raise
+        return wrapper
+    return decorator
+
+# Stack multiple concerns
+@traced("fetch_user_data")
+@with_timeout(30)
+@retry(stop=stop_after_attempt(3), wait=wait_exponential_jitter())
+async def fetch_user_data(user_id: str) -> dict:
+    """Fetch user with tracing, timeout, and retry."""
+    ...
+```
+
+### Pattern 8: Dependency Injection for Testability
+
+Pass infrastructure components through constructors for easy testing.
+
+```python
+from dataclasses import dataclass
+from typing import Protocol
+
+class Logger(Protocol):
+    def info(self, msg: str, **kwargs) -> None: ...
+    def error(self, msg: str, **kwargs) -> None: ...
+
+class MetricsClient(Protocol):
+    def increment(self, metric: str, tags: dict | None = None) -> None: ...
+    def timing(self, metric: str, value: float) -> None: ...
+
+@dataclass
+class UserService:
+    """Service with injected infrastructure."""
+
+    repository: UserRepository
+    logger: Logger
+    metrics: MetricsClient
+
+    async def get_user(self, user_id: str) -> User:
+        self.logger.info("Fetching user", user_id=user_id)
+        start = time.perf_counter()
+
+        try:
+            user = await self.repository.get(user_id)
+            self.metrics.increment("user.fetch.success")
+            return user
+        except Exception as e:
+            self.metrics.increment("user.fetch.error")
+            self.logger.error("Failed to fetch user", user_id=user_id, error=str(e))
+            raise
+        finally:
+            elapsed = time.perf_counter() - start
+            self.metrics.timing("user.fetch.duration", elapsed)
+
+# Easy to test with fakes
+service = UserService(
+    repository=FakeRepository(),
+    logger=FakeLogger(),
+    metrics=FakeMetrics(),
+)
+```
+
+### Pattern 9: Fail-Safe Defaults
+
+Degrade gracefully when non-critical operations fail.
+
+```python
+from typing import TypeVar
+from collections.abc import Callable
+
+T = TypeVar("T")
+
+def fail_safe(default: T, log_failure: bool = True):
+    """Return default value on failure instead of raising."""
+    def decorator(func: Callable[..., T]) -> Callable[..., T]:
+        @wraps(func)
+        async def wrapper(*args, **kwargs) -> T:
+            try:
+                return await func(*args, **kwargs)
+            except Exception as e:
+                if log_failure:
+                    logger.warning(
+                        "Operation failed, using default",
+                        function=func.__name__,
+                        error=str(e),
+                    )
+                return default
+        return wrapper
+    return decorator
+
+@fail_safe(default=[])
+async def get_recommendations(user_id: str) -> list[str]:
+    """Get recommendations, return empty list on failure."""
+    ...
+```
+
+## Best Practices Summary
+
+1. **Retry only transient errors** - Don't retry bugs or authentication failures
+2. **Use exponential backoff** - Give services time to recover
+3. **Add jitter** - Prevent thundering herd from synchronized retries
+4. **Cap total duration** - `stop_after_attempt(5) | stop_after_delay(60)`
+5. **Log every retry** - Silent retries hide systemic problems
+6. **Use decorators** - Keep retry logic separate from business logic
+7. **Inject dependencies** - Make infrastructure testable
+8. **Set timeouts everywhere** - Every network call needs a timeout
+9. **Fail gracefully** - Return cached/default values for non-critical paths
+10. **Monitor retry rates** - High retry rates indicate underlying issues
diff --git a/plugins/python-development/skills/python-resource-management/SKILL.md b/plugins/python-development/skills/python-resource-management/SKILL.md
new file mode 100644
index 0000000..dd9ce93
--- /dev/null
+++ b/plugins/python-development/skills/python-resource-management/SKILL.md
@@ -0,0 +1,421 @@
+---
+name: python-resource-management
+description: Python resource management with context managers, cleanup patterns, and streaming. Use when managing connections, file handles, implementing cleanup logic, or building streaming responses with accumulated state.
+---
+
+# Python Resource Management
+
+Manage resources deterministically using context managers. Resources like database connections, file handles, and network sockets should be released reliably, even when exceptions occur.
+
+## When to Use This Skill
+
+- Managing database connections and connection pools
+- Working with file handles and I/O
+- Implementing custom context managers
+- Building streaming responses with state
+- Handling nested resource cleanup
+- Creating async context managers
+
+## Core Concepts
+
+### 1. Context Managers
+
+The `with` statement ensures resources are released automatically, even on exceptions.
+
+### 2. Protocol Methods
+
+`__enter__`/`__exit__` for sync, `__aenter__`/`__aexit__` for async resource management.
+
+### 3. Unconditional Cleanup
+
+`__exit__` always runs, regardless of whether an exception occurred.
+
+### 4. Exception Handling
+
+Return `True` from `__exit__` to suppress exceptions, `False` to propagate them.
+
+## Quick Start
+
+```python
+from contextlib import contextmanager
+
+@contextmanager
+def managed_resource():
+    resource = acquire_resource()
+    try:
+        yield resource
+    finally:
+        resource.cleanup()
+
+with managed_resource() as r:
+    r.do_work()
+```
+
+## Fundamental Patterns
+
+### Pattern 1: Class-Based Context Manager
+
+Implement the context manager protocol for complex resources.
+
+```python
+class DatabaseConnection:
+    """Database connection with automatic cleanup."""
+
+    def __init__(self, dsn: str) -> None:
+        self._dsn = dsn
+        self._conn: Connection | None = None
+
+    def connect(self) -> None:
+        """Establish database connection."""
+        self._conn = psycopg.connect(self._dsn)
+
+    def close(self) -> None:
+        """Close connection if open."""
+        if self._conn is not None:
+            self._conn.close()
+            self._conn = None
+
+    def __enter__(self) -> "DatabaseConnection":
+        """Enter context: connect and return self."""
+        self.connect()
+        return self
+
+    def __exit__(
+        self,
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
+    ) -> None:
+        """Exit context: always close connection."""
+        self.close()
+
+# Usage with context manager (preferred)
+with DatabaseConnection(dsn) as db:
+    result = db.execute(query)
+
+# Manual management when needed
+db = DatabaseConnection(dsn)
+db.connect()
+try:
+    result = db.execute(query)
+finally:
+    db.close()
+```
+
+### Pattern 2: Async Context Manager
+
+For async resources, implement the async protocol.
+
+```python
+class AsyncDatabasePool:
+    """Async database connection pool."""
+
+    def __init__(self, dsn: str, min_size: int = 1, max_size: int = 10) -> None:
+        self._dsn = dsn
+        self._min_size = min_size
+        self._max_size = max_size
+        self._pool: asyncpg.Pool | None = None
+
+    async def __aenter__(self) -> "AsyncDatabasePool":
+        """Create connection pool."""
+        self._pool = await asyncpg.create_pool(
+            self._dsn,
+            min_size=self._min_size,
+            max_size=self._max_size,
+        )
+        return self
+
+    async def __aexit__(
+        self,
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
+    ) -> None:
+        """Close all connections in pool."""
+        if self._pool is not None:
+            await self._pool.close()
+
+    async def execute(self, query: str, *args) -> list[dict]:
+        """Execute query using pooled connection."""
+        async with self._pool.acquire() as conn:
+            return await conn.fetch(query, *args)
+
+# Usage
+async with AsyncDatabasePool(dsn) as pool:
+    users = await pool.execute("SELECT * FROM users WHERE active = $1", True)
+```
+
+### Pattern 3: Using @contextmanager Decorator
+
+Simplify context managers with the decorator for straightforward cases.
+
+```python
+from contextlib import contextmanager, asynccontextmanager
+import time
+import structlog
+
+logger = structlog.get_logger()
+
+@contextmanager
+def timed_block(name: str):
+    """Time a block of code."""
+    start = time.perf_counter()
+    try:
+        yield
+    finally:
+        elapsed = time.perf_counter() - start
+        logger.info(f"{name} completed", duration_seconds=round(elapsed, 3))
+
+# Usage
+with timed_block("data_processing"):
+    process_large_dataset()
+
+@asynccontextmanager
+async def database_transaction(conn: AsyncConnection):
+    """Manage database transaction."""
+    await conn.execute("BEGIN")
+    try:
+        yield conn
+        await conn.execute("COMMIT")
+    except Exception:
+        await conn.execute("ROLLBACK")
+        raise
+
+# Usage
+async with database_transaction(conn) as tx:
+    await tx.execute("INSERT INTO users ...")
+    await tx.execute("INSERT INTO audit_log ...")
+```
+
+### Pattern 4: Unconditional Resource Release
+
+Always clean up resources in `__exit__`, regardless of exceptions.
+
+```python
+class FileProcessor:
+    """Process file with guaranteed cleanup."""
+
+    def __init__(self, path: str) -> None:
+        self._path = path
+        self._file: IO | None = None
+        self._temp_files: list[Path] = []
+
+    def __enter__(self) -> "FileProcessor":
+        self._file = open(self._path, "r")
+        return self
+
+    def __exit__(
+        self,
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
+    ) -> None:
+        """Clean up all resources unconditionally."""
+        # Close main file
+        if self._file is not None:
+            self._file.close()
+
+        # Clean up any temporary files
+        for temp_file in self._temp_files:
+            try:
+                temp_file.unlink()
+            except OSError:
+                pass  # Best effort cleanup
+
+        # Return None/False to propagate any exception
+```
+
+## Advanced Patterns
+
+### Pattern 5: Selective Exception Suppression
+
+Only suppress specific, documented exceptions.
+
+```python
+class StreamWriter:
+    """Writer that handles broken pipe gracefully."""
+
+    def __init__(self, stream) -> None:
+        self._stream = stream
+
+    def __enter__(self) -> "StreamWriter":
+        return self
+
+    def __exit__(
+        self,
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
+    ) -> bool:
+        """Clean up, suppressing BrokenPipeError on shutdown."""
+        self._stream.close()
+
+        # Suppress BrokenPipeError (client disconnected)
+        # This is expected behavior, not an error
+        if exc_type is BrokenPipeError:
+            return True  # Exception suppressed
+
+        return False  # Propagate all other exceptions
+```
+
+### Pattern 6: Streaming with Accumulated State
+
+Maintain both incremental chunks and accumulated state during streaming.
+
+```python
+from collections.abc import Generator
+from dataclasses import dataclass, field
+
+@dataclass
+class StreamingResult:
+    """Accumulated streaming result."""
+
+    chunks: list[str] = field(default_factory=list)
+    _finalized: bool = False
+
+    @property
+    def content(self) -> str:
+        """Get accumulated content."""
+        return "".join(self.chunks)
+
+    def add_chunk(self, chunk: str) -> None:
+        """Add chunk to accumulator."""
+        if self._finalized:
+            raise RuntimeError("Cannot add to finalized result")
+        self.chunks.append(chunk)
+
+    def finalize(self) -> str:
+        """Mark stream complete and return content."""
+        self._finalized = True
+        return self.content
+
+def stream_with_accumulation(
+    response: StreamingResponse,
+) -> Generator[tuple[str, str], None, str]:
+    """Stream response while accumulating content.
+
+    Yields:
+        Tuple of (accumulated_content, new_chunk) for each chunk.
+
+    Returns:
+        Final accumulated content.
+    """
+    result = StreamingResult()
+
+    for chunk in response.iter_content():
+        result.add_chunk(chunk)
+        yield result.content, chunk
+
+    return result.finalize()
+```
+
+### Pattern 7: Efficient String Accumulation
+
+Avoid O(n²) string concatenation when accumulating.
+
+```python
+def accumulate_stream(stream) -> str:
+    """Efficiently accumulate stream content."""
+    # BAD: O(n²) due to string immutability
+    # content = ""
+    # for chunk in stream:
+    #     content += chunk  # Creates new string each time
+
+    # GOOD: O(n) with list and join
+    chunks: list[str] = []
+    for chunk in stream:
+        chunks.append(chunk)
+    return "".join(chunks)  # Single allocation
+```
+
+### Pattern 8: Tracking Stream Metrics
+
+Measure time-to-first-byte and total streaming time.
+
+```python
+import time
+from collections.abc import Generator
+
+def stream_with_metrics(
+    response: StreamingResponse,
+) -> Generator[str, None, dict]:
+    """Stream response while collecting metrics.
+
+    Yields:
+        Content chunks.
+
+    Returns:
+        Metrics dictionary.
+    """
+    start = time.perf_counter()
+    first_chunk_time: float | None = None
+    chunk_count = 0
+    total_bytes = 0
+
+    for chunk in response.iter_content():
+        if first_chunk_time is None:
+            first_chunk_time = time.perf_counter() - start
+
+        chunk_count += 1
+        total_bytes += len(chunk.encode())
+        yield chunk
+
+    total_time = time.perf_counter() - start
+
+    return {
+        "time_to_first_byte_ms": round((first_chunk_time or 0) * 1000, 2),
+        "total_time_ms": round(total_time * 1000, 2),
+        "chunk_count": chunk_count,
+        "total_bytes": total_bytes,
+    }
+```
+
+### Pattern 9: Managing Multiple Resources with ExitStack
+
+Handle a dynamic number of resources cleanly.
+
+```python
+from contextlib import ExitStack, AsyncExitStack
+from pathlib import Path
+
+def process_files(paths: list[Path]) -> list[str]:
+    """Process multiple files with automatic cleanup."""
+    results = []
+
+    with ExitStack() as stack:
+        # Open all files - they'll all be closed when block exits
+        files = [stack.enter_context(open(p)) for p in paths]
+
+        for f in files:
+            results.append(f.read())
+
+    return results
+
+async def process_connections(hosts: list[str]) -> list[dict]:
+    """Process multiple async connections."""
+    results = []
+
+    async with AsyncExitStack() as stack:
+        connections = [
+            await stack.enter_async_context(connect_to_host(host))
+            for host in hosts
+        ]
+
+        for conn in connections:
+            results.append(await conn.fetch_data())
+
+    return results
+```
+
+## Best Practices Summary
+
+1. **Always use context managers** - For any resource that needs cleanup
+2. **Clean up unconditionally** - `__exit__` runs even on exception
+3. **Don't suppress unexpectedly** - Return `False` unless suppression is intentional
+4. **Use @contextmanager** - For simple resource patterns
+5. **Implement both protocols** - Support `with` and manual management
+6. **Use ExitStack** - For dynamic numbers of resources
+7. **Accumulate efficiently** - List + join, not string concatenation
+8. **Track metrics** - Time-to-first-byte matters for streaming
+9. **Document behavior** - Especially exception suppression
+10. **Test cleanup paths** - Verify resources are released on errors
diff --git a/plugins/python-development/skills/python-testing-patterns/SKILL.md b/plugins/python-development/skills/python-testing-patterns/SKILL.md
index 23ade50..6693894 100644
--- a/plugins/python-development/skills/python-testing-patterns/SKILL.md
+++ b/plugins/python-development/skills/python-testing-patterns/SKILL.md
@@ -618,6 +618,52 @@ def test_sorted_list_properties(lst):
         assert sorted_lst[i] <= sorted_lst[i + 1]
 ```
 
+## Test Design Principles
+
+### One Behavior Per Test
+
+Each test should verify exactly one behavior. This makes failures easy to diagnose and tests easy to maintain.
+
+```python
+# BAD - testing multiple behaviors
+def test_user_service():
+    user = service.create_user(data)
+    assert user.id is not None
+    assert user.email == data["email"]
+    updated = service.update_user(user.id, {"name": "New"})
+    assert updated.name == "New"
+
+# GOOD - focused tests
+def test_create_user_assigns_id():
+    user = service.create_user(data)
+    assert user.id is not None
+
+def test_create_user_stores_email():
+    user = service.create_user(data)
+    assert user.email == data["email"]
+
+def test_update_user_changes_name():
+    user = service.create_user(data)
+    updated = service.update_user(user.id, {"name": "New"})
+    assert updated.name == "New"
+```
+
+### Test Error Paths
+
+Always test failure cases, not just happy paths.
+
+```python
+def test_get_user_raises_not_found():
+    with pytest.raises(UserNotFoundError) as exc_info:
+        service.get_user("nonexistent-id")
+
+    assert "nonexistent-id" in str(exc_info.value)
+
+def test_create_user_rejects_invalid_email():
+    with pytest.raises(ValueError, match="Invalid email format"):
+        service.create_user({"email": "not-an-email"})
+```
+
 ## Testing Best Practices
 
 ### Test Organization
@@ -636,38 +682,131 @@ def test_sorted_list_properties(lst):
 #     test_workflows.py
 ```
 
-### Test Naming
+### Test Naming Convention
+
+A common pattern: `test_<unit>_<scenario>_<expected_outcome>`. Adapt to your team's preferences.
 
 ```python
-# Good test names
+# Pattern: test_<unit>_<scenario>_<expected>
+def test_create_user_with_valid_data_returns_user():
+    ...
+
+def test_create_user_with_duplicate_email_raises_conflict():
+    ...
+
+def test_get_user_with_unknown_id_returns_none():
+    ...
+
+# Good test names - clear and descriptive
 def test_user_creation_with_valid_data():
     """Clear name describes what is being tested."""
     pass
 
-
 def test_login_fails_with_invalid_password():
     """Name describes expected behavior."""
     pass
 
-
 def test_api_returns_404_for_missing_resource():
     """Specific about inputs and expected outcomes."""
     pass
 
-
-# Bad test names
+# Bad test names - avoid these
 def test_1():  # Not descriptive
     pass
 
-
 def test_user():  # Too vague
     pass
 
-
 def test_function():  # Doesn't explain what's tested
     pass
 ```
 
+### Testing Retry Behavior
+
+Verify that retry logic works correctly using mock side effects.
+
+```python
+from unittest.mock import Mock
+
+def test_retries_on_transient_error():
+    """Test that service retries on transient failures."""
+    client = Mock()
+    # Fail twice, then succeed
+    client.request.side_effect = [
+        ConnectionError("Failed"),
+        ConnectionError("Failed"),
+        {"status": "ok"},
+    ]
+
+    service = ServiceWithRetry(client, max_retries=3)
+    result = service.fetch()
+
+    assert result == {"status": "ok"}
+    assert client.request.call_count == 3
+
+def test_gives_up_after_max_retries():
+    """Test that service stops retrying after max attempts."""
+    client = Mock()
+    client.request.side_effect = ConnectionError("Failed")
+
+    service = ServiceWithRetry(client, max_retries=3)
+
+    with pytest.raises(ConnectionError):
+        service.fetch()
+
+    assert client.request.call_count == 3
+
+def test_does_not_retry_on_permanent_error():
+    """Test that permanent errors are not retried."""
+    client = Mock()
+    client.request.side_effect = ValueError("Invalid input")
+
+    service = ServiceWithRetry(client, max_retries=3)
+
+    with pytest.raises(ValueError):
+        service.fetch()
+
+    # Only called once - no retry for ValueError
+    assert client.request.call_count == 1
+```
+
+### Mocking Time with Freezegun
+
+Use freezegun to control time in tests for predictable time-dependent behavior.
+
+```python
+from freezegun import freeze_time
+from datetime import datetime, timedelta
+
+@freeze_time("2026-01-15 10:00:00")
+def test_token_expiry():
+    """Test token expires at correct time."""
+    token = create_token(expires_in_seconds=3600)
+    assert token.expires_at == datetime(2026, 1, 15, 11, 0, 0)
+
+@freeze_time("2026-01-15 10:00:00")
+def test_is_expired_returns_false_before_expiry():
+    """Test token is not expired when within validity period."""
+    token = create_token(expires_in_seconds=3600)
+    assert not token.is_expired()
+
+@freeze_time("2026-01-15 12:00:00")
+def test_is_expired_returns_true_after_expiry():
+    """Test token is expired after validity period."""
+    token = Token(expires_at=datetime(2026, 1, 15, 11, 30, 0))
+    assert token.is_expired()
+
+def test_with_time_travel():
+    """Test behavior across time using freeze_time context."""
+    with freeze_time("2026-01-01") as frozen_time:
+        item = create_item()
+        assert item.created_at == datetime(2026, 1, 1)
+
+        # Move forward in time
+        frozen_time.move_to("2026-01-15")
+        assert item.age_days == 14
+```
+
 ### Test Markers
 
 ```python
diff --git a/plugins/python-development/skills/python-type-safety/SKILL.md b/plugins/python-development/skills/python-type-safety/SKILL.md
new file mode 100644
index 0000000..99ad437
--- /dev/null
+++ b/plugins/python-development/skills/python-type-safety/SKILL.md
@@ -0,0 +1,428 @@
+---
+name: python-type-safety
+description: Python type safety with type hints, generics, protocols, and strict type checking. Use when adding type annotations, implementing generic classes, defining structural interfaces, or configuring mypy/pyright.
+---
+
+# Python Type Safety
+
+Leverage Python's type system to catch errors at static analysis time. Type annotations serve as enforced documentation that tooling validates automatically.
+
+## When to Use This Skill
+
+- Adding type hints to existing code
+- Creating generic, reusable classes
+- Defining structural interfaces with protocols
+- Configuring mypy or pyright for strict checking
+- Understanding type narrowing and guards
+- Building type-safe APIs and libraries
+
+## Core Concepts
+
+### 1. Type Annotations
+
+Declare expected types for function parameters, return values, and variables.
+
+### 2. Generics
+
+Write reusable code that preserves type information across different types.
+
+### 3. Protocols
+
+Define structural interfaces without inheritance (duck typing with type safety).
+
+### 4. Type Narrowing
+
+Use guards and conditionals to narrow types within code blocks.
+
+## Quick Start
+
+```python
+def get_user(user_id: str) -> User | None:
+    """Return type makes 'might not exist' explicit."""
+    ...
+
+# Type checker enforces handling None case
+user = get_user("123")
+if user is None:
+    raise UserNotFoundError("123")
+print(user.name)  # Type checker knows user is User here
+```
+
+## Fundamental Patterns
+
+### Pattern 1: Annotate All Public Signatures
+
+Every public function, method, and class should have type annotations.
+
+```python
+def get_user(user_id: str) -> User:
+    """Retrieve user by ID."""
+    ...
+
+def process_batch(
+    items: list[Item],
+    max_workers: int = 4,
+) -> BatchResult[ProcessedItem]:
+    """Process items concurrently."""
+    ...
+
+class UserRepository:
+    def __init__(self, db: Database) -> None:
+        self._db = db
+
+    async def find_by_id(self, user_id: str) -> User | None:
+        """Return User if found, None otherwise."""
+        ...
+
+    async def find_by_email(self, email: str) -> User | None:
+        ...
+
+    async def save(self, user: User) -> User:
+        """Save and return user with generated ID."""
+        ...
+```
+
+Use `mypy --strict` or `pyright` in CI to catch type errors early. For existing projects, enable strict mode incrementally using per-module overrides.
+
+### Pattern 2: Use Modern Union Syntax
+
+Python 3.10+ provides cleaner union syntax.
+
+```python
+# Preferred (3.10+)
+def find_user(user_id: str) -> User | None:
+    ...
+
+def parse_value(v: str) -> int | float | str:
+    ...
+
+# Older style (still valid, needed for 3.9)
+from typing import Optional, Union
+
+def find_user(user_id: str) -> Optional[User]:
+    ...
+```
+
+### Pattern 3: Type Narrowing with Guards
+
+Use conditionals to narrow types for the type checker.
+
+```python
+def process_user(user_id: str) -> UserData:
+    user = find_user(user_id)
+
+    if user is None:
+        raise UserNotFoundError(f"User {user_id} not found")
+
+    # Type checker knows user is User here, not User | None
+    return UserData(
+        name=user.name,
+        email=user.email,
+    )
+
+def process_items(items: list[Item | None]) -> list[ProcessedItem]:
+    # Filter and narrow types
+    valid_items = [item for item in items if item is not None]
+    # valid_items is now list[Item]
+    return [process(item) for item in valid_items]
+```
+
+### Pattern 4: Generic Classes
+
+Create type-safe reusable containers.
+
+```python
+from typing import TypeVar, Generic
+
+T = TypeVar("T")
+E = TypeVar("E", bound=Exception)
+
+class Result(Generic[T, E]):
+    """Represents either a success value or an error."""
+
+    def __init__(
+        self,
+        value: T | None = None,
+        error: E | None = None,
+    ) -> None:
+        if (value is None) == (error is None):
+            raise ValueError("Exactly one of value or error must be set")
+        self._value = value
+        self._error = error
+
+    @property
+    def is_success(self) -> bool:
+        return self._error is None
+
+    @property
+    def is_failure(self) -> bool:
+        return self._error is not None
+
+    def unwrap(self) -> T:
+        """Get value or raise the error."""
+        if self._error is not None:
+            raise self._error
+        return self._value  # type: ignore[return-value]
+
+    def unwrap_or(self, default: T) -> T:
+        """Get value or return default."""
+        if self._error is not None:
+            return default
+        return self._value  # type: ignore[return-value]
+
+# Usage preserves types
+def parse_config(path: str) -> Result[Config, ConfigError]:
+    try:
+        return Result(value=Config.from_file(path))
+    except ConfigError as e:
+        return Result(error=e)
+
+result = parse_config("config.yaml")
+if result.is_success:
+    config = result.unwrap()  # Type: Config
+```
+
+## Advanced Patterns
+
+### Pattern 5: Generic Repository
+
+Create type-safe data access patterns.
+
+```python
+from typing import TypeVar, Generic
+from abc import ABC, abstractmethod
+
+T = TypeVar("T")
+ID = TypeVar("ID")
+
+class Repository(ABC, Generic[T, ID]):
+    """Generic repository interface."""
+
+    @abstractmethod
+    async def get(self, id: ID) -> T | None:
+        """Get entity by ID."""
+        ...
+
+    @abstractmethod
+    async def save(self, entity: T) -> T:
+        """Save and return entity."""
+        ...
+
+    @abstractmethod
+    async def delete(self, id: ID) -> bool:
+        """Delete entity, return True if existed."""
+        ...
+
+class UserRepository(Repository[User, str]):
+    """Concrete repository for Users with string IDs."""
+
+    async def get(self, id: str) -> User | None:
+        row = await self._db.fetchrow(
+            "SELECT * FROM users WHERE id = $1", id
+        )
+        return User(**row) if row else None
+
+    async def save(self, entity: User) -> User:
+        ...
+
+    async def delete(self, id: str) -> bool:
+        ...
+```
+
+### Pattern 6: TypeVar with Bounds
+
+Restrict generic parameters to specific types.
+
+```python
+from typing import TypeVar
+from pydantic import BaseModel
+
+ModelT = TypeVar("ModelT", bound=BaseModel)
+
+def validate_and_create(model_cls: type[ModelT], data: dict) -> ModelT:
+    """Create a validated Pydantic model from dict."""
+    return model_cls.model_validate(data)
+
+# Works with any BaseModel subclass
+class User(BaseModel):
+    name: str
+    email: str
+
+user = validate_and_create(User, {"name": "Alice", "email": "a@b.com"})
+# user is typed as User
+
+# Type error: str is not a BaseModel subclass
+result = validate_and_create(str, {"name": "Alice"})  # Error!
+```
+
+### Pattern 7: Protocols for Structural Typing
+
+Define interfaces without requiring inheritance.
+
+```python
+from typing import Protocol, runtime_checkable
+
+@runtime_checkable
+class Serializable(Protocol):
+    """Any class that can be serialized to/from dict."""
+
+    def to_dict(self) -> dict:
+        ...
+
+    @classmethod
+    def from_dict(cls, data: dict) -> "Serializable":
+        ...
+
+# User satisfies Serializable without inheriting from it
+class User:
+    def __init__(self, id: str, name: str) -> None:
+        self.id = id
+        self.name = name
+
+    def to_dict(self) -> dict:
+        return {"id": self.id, "name": self.name}
+
+    @classmethod
+    def from_dict(cls, data: dict) -> "User":
+        return cls(id=data["id"], name=data["name"])
+
+def serialize(obj: Serializable) -> str:
+    """Works with any Serializable object."""
+    return json.dumps(obj.to_dict())
+
+# Works - User matches the protocol
+serialize(User("1", "Alice"))
+
+# Runtime checking with @runtime_checkable
+isinstance(User("1", "Alice"), Serializable)  # True
+```
+
+### Pattern 8: Common Protocol Patterns
+
+Define reusable structural interfaces.
+
+```python
+from typing import Protocol
+
+class Closeable(Protocol):
+    """Resource that can be closed."""
+    def close(self) -> None: ...
+
+class AsyncCloseable(Protocol):
+    """Async resource that can be closed."""
+    async def close(self) -> None: ...
+
+class Readable(Protocol):
+    """Object that can be read from."""
+    def read(self, n: int = -1) -> bytes: ...
+
+class HasId(Protocol):
+    """Object with an ID property."""
+    @property
+    def id(self) -> str: ...
+
+class Comparable(Protocol):
+    """Object that supports comparison."""
+    def __lt__(self, other: "Comparable") -> bool: ...
+    def __le__(self, other: "Comparable") -> bool: ...
+```
+
+### Pattern 9: Type Aliases
+
+Create meaningful type names.
+
+**Note:** The `type` statement was introduced in Python 3.10 for simple aliases. Generic type statements require Python 3.12+.
+
+```python
+# Python 3.10+ type statement for simple aliases
+type UserId = str
+type UserDict = dict[str, Any]
+
+# Python 3.12+ type statement with generics
+type Handler[T] = Callable[[Request], T]
+type AsyncHandler[T] = Callable[[Request], Awaitable[T]]
+
+# Python 3.9-3.11 style (needed for broader compatibility)
+from typing import TypeAlias
+from collections.abc import Callable, Awaitable
+
+UserId: TypeAlias = str
+Handler: TypeAlias = Callable[[Request], Response]
+
+# Usage
+def register_handler(path: str, handler: Handler[Response]) -> None:
+    ...
+```
+
+### Pattern 10: Callable Types
+
+Type function parameters and callbacks.
+
+```python
+from collections.abc import Callable, Awaitable
+
+# Sync callback
+ProgressCallback = Callable[[int, int], None]  # (current, total)
+
+# Async callback
+AsyncHandler = Callable[[Request], Awaitable[Response]]
+
+# With named parameters (using Protocol)
+class OnProgress(Protocol):
+    def __call__(
+        self,
+        current: int,
+        total: int,
+        *,
+        message: str = "",
+    ) -> None: ...
+
+def process_items(
+    items: list[Item],
+    on_progress: ProgressCallback | None = None,
+) -> list[Result]:
+    for i, item in enumerate(items):
+        if on_progress:
+            on_progress(i, len(items))
+        ...
+```
+
+## Configuration
+
+### Strict Mode Checklist
+
+For `mypy --strict` compliance:
+
+```toml
+# pyproject.toml
+[tool.mypy]
+python_version = "3.12"
+strict = true
+warn_return_any = true
+warn_unused_ignores = true
+disallow_untyped_defs = true
+disallow_incomplete_defs = true
+no_implicit_optional = true
+```
+
+Incremental adoption goals:
+- All function parameters annotated
+- All return types annotated
+- Class attributes annotated
+- Minimize `Any` usage (acceptable for truly dynamic data)
+- Generic collections use type parameters (`list[str]` not `list`)
+
+For existing codebases, enable strict mode per-module using `# mypy: strict` or configure per-module overrides in `pyproject.toml`.
+
+## Best Practices Summary
+
+1. **Annotate all public APIs** - Functions, methods, class attributes
+2. **Use `T | None`** - Modern union syntax over `Optional[T]`
+3. **Run strict type checking** - `mypy --strict` in CI
+4. **Use generics** - Preserve type info in reusable code
+5. **Define protocols** - Structural typing for interfaces
+6. **Narrow types** - Use guards to help the type checker
+7. **Bound type vars** - Restrict generics to meaningful types
+8. **Create type aliases** - Meaningful names for complex types
+9. **Minimize `Any`** - Use specific types or generics. `Any` is acceptable for truly dynamic data or when interfacing with untyped third-party code
+10. **Document with types** - Types are enforceable documentation