fix: replace (str, Enum) with StrEnum to resolve ruff UP042

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

conftest.py

@@ -0,0 +1,14 @@
+"""Pytest configuration for the polymarket-insider-tracker tests."""
+
+import pytest
+
+# Configure pytest-asyncio
+pytest_plugins = ["pytest_asyncio"]
+
+
+@pytest.fixture(scope="session")
+def event_loop_policy():
+    """Use default event loop policy."""
+    import asyncio
+
+    return asyncio.DefaultEventLoopPolicy()

pyproject.toml

@@ -12,6 +12,7 @@ dependencies = [
     "sqlalchemy>=2.0.0",
     "alembic>=1.13.0",
     "pydantic>=2.0.0",
+    "pydantic-settings>=2.0.0",
     "python-dotenv>=1.0.0",
     "websockets>=12.0",
     "prometheus-client>=0.19.0",

src/polymarket_insider_tracker/__main__.py

@@ -0,0 +1,302 @@
+"""CLI entry point for Polymarket Insider Tracker.
+
+This module provides the main entry point for running the tracker
+from the command line.
+
+Usage:
+    python -m polymarket_insider_tracker [options]
+"""
+
+from __future__ import annotations
+
+import argparse
+import asyncio
+import logging
+import logging.config
+import sys
+from typing import NoReturn
+
+from pydantic import ValidationError
+
+from polymarket_insider_tracker import __version__
+from polymarket_insider_tracker.config import Settings, clear_settings_cache, get_settings
+from polymarket_insider_tracker.pipeline import Pipeline
+from polymarket_insider_tracker.shutdown import GracefulShutdown
+
+# Application info
+APP_NAME = "Polymarket Insider Tracker"
+APP_VERSION = __version__
+
+# Exit codes
+EXIT_SUCCESS = 0
+EXIT_ERROR = 1
+EXIT_CONFIG_ERROR = 2
+EXIT_INTERRUPTED = 130
+
+
+def create_parser() -> argparse.ArgumentParser:
+    """Create the argument parser for the CLI.
+
+    Returns:
+        Configured ArgumentParser instance.
+    """
+    parser = argparse.ArgumentParser(
+        prog="polymarket-insider-tracker",
+        description="Detect insider trading activity on Polymarket prediction markets.",
+        formatter_class=argparse.RawDescriptionHelpFormatter,
+        epilog="""
+Examples:
+  python -m polymarket_insider_tracker           Run full pipeline
+  python -m polymarket_insider_tracker --config-check  Validate config and exit
+  python -m polymarket_insider_tracker --dry-run       Run without sending alerts
+  python -m polymarket_insider_tracker --log-level DEBUG  Enable debug logging
+        """,
+    )
+
+    parser.add_argument(
+        "--version",
+        action="version",
+        version=f"%(prog)s {APP_VERSION}",
+    )
+
+    parser.add_argument(
+        "--config-check",
+        action="store_true",
+        help="Validate configuration and exit without running pipeline",
+    )
+
+    parser.add_argument(
+        "--log-level",
+        choices=["DEBUG", "INFO", "WARNING", "ERROR", "CRITICAL"],
+        default=None,
+        help="Override logging level (default: from settings)",
+    )
+
+    parser.add_argument(
+        "--dry-run",
+        action="store_true",
+        help="Run pipeline but don't send alerts",
+    )
+
+    parser.add_argument(
+        "--health-port",
+        type=int,
+        default=None,
+        help="Override health check port (default: from settings)",
+    )
+
+    return parser
+
+
+def configure_logging(level: str) -> None:
+    """Configure structured logging for the application.
+
+    Args:
+        level: Logging level string (DEBUG, INFO, etc.)
+    """
+    config = {
+        "version": 1,
+        "disable_existing_loggers": False,
+        "formatters": {
+            "standard": {
+                "format": "%(asctime)s [%(levelname)s] %(name)s: %(message)s",
+                "datefmt": "%Y-%m-%d %H:%M:%S",
+            },
+            "detailed": {
+                "format": (
+                    "%(asctime)s [%(levelname)s] %(name)s (%(filename)s:%(lineno)d): %(message)s"
+                ),
+                "datefmt": "%Y-%m-%d %H:%M:%S",
+            },
+        },
+        "handlers": {
+            "console": {
+                "class": "logging.StreamHandler",
+                "level": level,
+                "formatter": "detailed" if level == "DEBUG" else "standard",
+                "stream": "ext://sys.stdout",
+            },
+        },
+        "root": {
+            "level": level,
+            "handlers": ["console"],
+        },
+        # Quieter logging for noisy libraries
+        "loggers": {
+            "httpx": {"level": "WARNING"},
+            "httpcore": {"level": "WARNING"},
+            "websockets": {"level": "WARNING"},
+            "web3": {"level": "WARNING"},
+            "urllib3": {"level": "WARNING"},
+        },
+    }
+    logging.config.dictConfig(config)
+
+
+def print_banner() -> None:
+    """Print the application startup banner."""
+    banner = f"""
+╔══════════════════════════════════════════════════════════════╗
+║                                                              ║
+║   {APP_NAME:^56}   ║
+║   {"v" + APP_VERSION:^56}   ║
+║                                                              ║
+╚══════════════════════════════════════════════════════════════╝
+"""
+    print(banner)
+
+
+def print_config_summary(settings: Settings, dry_run: bool) -> None:
+    """Print a summary of the configuration.
+
+    Args:
+        settings: Application settings.
+        dry_run: Whether dry-run mode is enabled.
+    """
+    summary = settings.redacted_summary()
+    print("Configuration:")
+    print(f"  Database: {summary['database_url']}")
+    print(f"  Redis: {summary['redis_url']}")
+    print(f"  Log Level: {summary['log_level']}")
+    print(f"  Health Port: {summary['health_port']}")
+    print(f"  Dry Run: {dry_run}")
+    print(f"  Discord: {'enabled' if summary['discord_enabled'] == 'True' else 'disabled'}")
+    print(f"  Telegram: {'enabled' if summary['telegram_enabled'] == 'True' else 'disabled'}")
+    print()
+
+
+def validate_config() -> Settings | None:
+    """Validate and load configuration.
+
+    Returns:
+        Settings instance if valid, None if invalid.
+    """
+    try:
+        # Clear cache to force reload
+        clear_settings_cache()
+        return get_settings()
+    except ValidationError as e:
+        print("Configuration validation failed:", file=sys.stderr)
+        for error in e.errors():
+            field = ".".join(str(loc) for loc in error["loc"])
+            msg = error["msg"]
+            print(f"  {field}: {msg}", file=sys.stderr)
+        return None
+
+
+def run_config_check(settings: Settings) -> int:
+    """Run configuration check and exit.
+
+    Args:
+        settings: Validated settings.
+
+    Returns:
+        Exit code (0 for success).
+    """
+    print("Configuration is valid!")
+    print()
+    print_config_summary(settings, dry_run=False)
+
+    # Test component availability
+    print("Checking component availability...")
+
+    # Check Discord
+    if settings.discord.enabled:
+        print("  Discord: configured")
+    else:
+        print("  Discord: not configured")
+
+    # Check Telegram
+    if settings.telegram.enabled:
+        print("  Telegram: configured")
+    else:
+        print("  Telegram: not configured")
+
+    print()
+    print("All checks passed. Ready to run.")
+    return EXIT_SUCCESS
+
+
+async def run_pipeline(
+    settings: Settings,
+    dry_run: bool,
+    shutdown_timeout: float = 30.0,
+) -> int:
+    """Run the main pipeline with graceful shutdown handling.
+
+    Args:
+        settings: Application settings.
+        dry_run: Whether to skip sending alerts.
+        shutdown_timeout: Maximum time to wait for graceful shutdown.
+
+    Returns:
+        Exit code.
+    """
+    logger = logging.getLogger(__name__)
+    shutdown = GracefulShutdown(timeout=shutdown_timeout)
+
+    try:
+        async with shutdown:
+            pipeline = Pipeline(settings, dry_run=dry_run)
+
+            # Register pipeline cleanup
+            shutdown.register_cleanup(pipeline.stop)
+
+            logger.info("Starting pipeline...")
+            await pipeline.start()
+
+            logger.info("Pipeline running. Press Ctrl+C to stop.")
+
+            # Wait for shutdown signal
+            await shutdown.wait()
+
+            logger.info("Shutdown signal received, stopping pipeline...")
+            await pipeline.stop()
+
+        return EXIT_SUCCESS
+    except KeyboardInterrupt:
+        logger.info("Interrupted by user")
+        return EXIT_INTERRUPTED
+    except Exception as e:
+        logger.exception("Pipeline failed: %s", e)
+        return EXIT_ERROR
+
+
+def main(argv: list[str] | None = None) -> NoReturn:
+    """Main entry point for the CLI.
+
+    Args:
+        argv: Command line arguments (defaults to sys.argv[1:]).
+    """
+    parser = create_parser()
+    args = parser.parse_args(argv)
+
+    # Validate configuration first
+    settings = validate_config()
+    if settings is None:
+        sys.exit(EXIT_CONFIG_ERROR)
+
+    # Determine effective log level
+    log_level = args.log_level or settings.log_level
+    configure_logging(log_level)
+
+    # Print banner
+    print_banner()
+
+    # Config check mode
+    if args.config_check:
+        sys.exit(run_config_check(settings))
+
+    # Determine dry-run mode
+    dry_run = args.dry_run or settings.dry_run
+
+    # Print config summary
+    print_config_summary(settings, dry_run)
+
+    # Run pipeline
+    exit_code = asyncio.run(run_pipeline(settings, dry_run))
+    sys.exit(exit_code)
+
+
+if __name__ == "__main__":
+    main()

src/polymarket_insider_tracker/alerter/formatter.py

@@ -190,10 +190,11 @@ class AlertFormatter:
         wallet_age_str = ""
         if assessment.fresh_wallet_signal:
             age_hours = assessment.fresh_wallet_signal.wallet_profile.age_hours
-            if age_hours < 1:
+            if age_hours is not None:
-                wallet_age_str = f" (Age: {int(age_hours * 60)}m)"
+                if age_hours < 1:
-            else:
+                    wallet_age_str = f" (Age: {int(age_hours * 60)}m)"
-                wallet_age_str = f" (Age: {age_hours:.0f}h)"
+                else:
+                    wallet_age_str = f" (Age: {age_hours:.0f}h)"
 
         fields: list[dict[str, object]] = [
             {
@@ -282,10 +283,11 @@ class AlertFormatter:
         wallet_line = f"*Wallet:* `{wallet_short}`"
         if assessment.fresh_wallet_signal:
             age_hours = assessment.fresh_wallet_signal.wallet_profile.age_hours
-            if age_hours < 1:
+            if age_hours is not None:
-                wallet_line += f" \\(Age: {int(age_hours * 60)}m\\)"
+                if age_hours < 1:
-            else:
+                    wallet_line += f" \\(Age: {int(age_hours * 60)}m\\)"
-                wallet_line += f" \\(Age: {age_hours:.0f}h\\)"
+                else:
+                    wallet_line += f" \\(Age: {age_hours:.0f}h\\)"
         lines.append(wallet_line)
 
         # Risk score
@@ -366,10 +368,11 @@ class AlertFormatter:
         wallet_line = f"Wallet: {wallet_short}"
         if assessment.fresh_wallet_signal:
             age_hours = assessment.fresh_wallet_signal.wallet_profile.age_hours
-            if age_hours < 1:
+            if age_hours is not None:
-                wallet_line += f" (Age: {int(age_hours * 60)}m)"
+                if age_hours < 1:
-            else:
+                    wallet_line += f" (Age: {int(age_hours * 60)}m)"
-                wallet_line += f" (Age: {age_hours:.0f}h)"
+                else:
+                    wallet_line += f" (Age: {age_hours:.0f}h)"
         lines.append(wallet_line)
 
         # Risk

src/polymarket_insider_tracker/alerter/history.py

@@ -362,7 +362,7 @@ class AlertHistory:
             start.timestamp(),
             end.timestamp(),
         )
-        return count
+        return int(count)
 
     async def cleanup_old_alerts(self) -> int:
         """Remove alerts older than retention period.
@@ -393,4 +393,4 @@ class AlertHistory:
         # Note: Individual alert records will expire via TTL
         # Wallet/market indexes will also expire via TTL
         logger.info(f"Cleaned up {removed} old alert references")
-        return removed
+        return int(removed)

src/polymarket_insider_tracker/config.py

@@ -0,0 +1,263 @@
+"""Configuration management service with Pydantic Settings.
+
+This module provides centralized configuration management for the
+Polymarket Insider Tracker application, loading and validating
+environment variables at startup.
+"""
+
+from __future__ import annotations
+
+import logging
+from functools import lru_cache
+from typing import Literal
+
+from pydantic import Field, SecretStr, field_validator
+from pydantic_settings import BaseSettings, SettingsConfigDict
+
+
+class DatabaseSettings(BaseSettings):
+    """Database connection settings."""
+
+    model_config = SettingsConfigDict(env_prefix="")
+
+    url: str = Field(
+        alias="DATABASE_URL",
+        description="PostgreSQL connection string",
+    )
+
+    @field_validator("url")
+    @classmethod
+    def validate_url(cls, v: str) -> str:
+        """Validate database URL format."""
+        if not v.startswith(("postgresql://", "postgresql+asyncpg://")):
+            raise ValueError("DATABASE_URL must be a PostgreSQL connection string")
+        return v
+
+
+class RedisSettings(BaseSettings):
+    """Redis connection settings."""
+
+    model_config = SettingsConfigDict(env_prefix="")
+
+    url: str = Field(
+        default="redis://localhost:6379",
+        alias="REDIS_URL",
+        description="Redis connection string",
+    )
+
+    @field_validator("url")
+    @classmethod
+    def validate_url(cls, v: str) -> str:
+        """Validate Redis URL format."""
+        if not v.startswith("redis://"):
+            raise ValueError("REDIS_URL must start with redis://")
+        return v
+
+
+class PolygonSettings(BaseSettings):
+    """Polygon blockchain RPC settings."""
+
+    model_config = SettingsConfigDict(env_prefix="POLYGON_")
+
+    rpc_url: str = Field(
+        default="https://polygon-rpc.com",
+        alias="POLYGON_RPC_URL",
+        description="Primary Polygon RPC endpoint",
+    )
+    fallback_rpc_url: str | None = Field(
+        default=None,
+        alias="POLYGON_FALLBACK_RPC_URL",
+        description="Fallback Polygon RPC endpoint",
+    )
+
+    @field_validator("rpc_url", "fallback_rpc_url")
+    @classmethod
+    def validate_url(cls, v: str | None) -> str | None:
+        """Validate RPC URL format."""
+        if v is None:
+            return v
+        if not v.startswith(("http://", "https://")):
+            raise ValueError("RPC URL must be an HTTP(S) endpoint")
+        return v
+
+
+class PolymarketSettings(BaseSettings):
+    """Polymarket API settings."""
+
+    model_config = SettingsConfigDict(env_prefix="POLYMARKET_")
+
+    ws_url: str = Field(
+        default="wss://ws-subscriptions-clob.polymarket.com/ws/market",
+        alias="POLYMARKET_WS_URL",
+        description="Polymarket WebSocket URL for live data",
+    )
+    api_key: SecretStr | None = Field(
+        default=None,
+        alias="POLYMARKET_API_KEY",
+        description="Optional Polymarket API key",
+    )
+
+    @field_validator("ws_url")
+    @classmethod
+    def validate_ws_url(cls, v: str) -> str:
+        """Validate WebSocket URL format."""
+        if not v.startswith(("ws://", "wss://")):
+            raise ValueError("WebSocket URL must start with ws:// or wss://")
+        return v
+
+
+class DiscordSettings(BaseSettings):
+    """Discord notification settings."""
+
+    model_config = SettingsConfigDict(env_prefix="DISCORD_")
+
+    webhook_url: SecretStr | None = Field(
+        default=None,
+        alias="DISCORD_WEBHOOK_URL",
+        description="Discord webhook URL for alerts",
+    )
+
+    @property
+    def enabled(self) -> bool:
+        """Check if Discord notifications are enabled."""
+        return self.webhook_url is not None
+
+
+class TelegramSettings(BaseSettings):
+    """Telegram notification settings."""
+
+    model_config = SettingsConfigDict(env_prefix="TELEGRAM_")
+
+    bot_token: SecretStr | None = Field(
+        default=None,
+        alias="TELEGRAM_BOT_TOKEN",
+        description="Telegram bot token",
+    )
+    chat_id: str | None = Field(
+        default=None,
+        alias="TELEGRAM_CHAT_ID",
+        description="Telegram chat ID for alerts",
+    )
+
+    @property
+    def enabled(self) -> bool:
+        """Check if Telegram notifications are enabled."""
+        return self.bot_token is not None and self.chat_id is not None
+
+
+class Settings(BaseSettings):
+    """Main application settings.
+
+    Loads configuration from environment variables with support for
+    .env files via python-dotenv.
+
+    Example:
+        ```python
+        from polymarket_insider_tracker.config import get_settings
+
+        settings = get_settings()
+        print(settings.database.url)
+        print(settings.log_level)
+        ```
+    """
+
+    model_config = SettingsConfigDict(
+        env_file=".env",
+        env_file_encoding="utf-8",
+        extra="ignore",
+    )
+
+    # Nested configuration groups
+    database: DatabaseSettings = Field(default_factory=DatabaseSettings)
+    redis: RedisSettings = Field(default_factory=RedisSettings)
+    polygon: PolygonSettings = Field(default_factory=PolygonSettings)
+    polymarket: PolymarketSettings = Field(default_factory=PolymarketSettings)
+    discord: DiscordSettings = Field(default_factory=DiscordSettings)
+    telegram: TelegramSettings = Field(default_factory=TelegramSettings)
+
+    # Application settings
+    log_level: Literal["DEBUG", "INFO", "WARNING", "ERROR", "CRITICAL"] = Field(
+        default="INFO",
+        alias="LOG_LEVEL",
+        description="Logging level",
+    )
+    health_port: int = Field(
+        default=8080,
+        alias="HEALTH_PORT",
+        description="HTTP port for health check endpoints",
+        ge=1,
+        le=65535,
+    )
+    dry_run: bool = Field(
+        default=False,
+        alias="DRY_RUN",
+        description="Run without sending actual alerts",
+    )
+
+    def get_logging_level(self) -> int:
+        """Get the numeric logging level."""
+        level: int = getattr(logging, self.log_level)
+        return level
+
+    def redacted_summary(self) -> dict[str, str | dict[str, str]]:
+        """Get a summary of settings with secrets redacted.
+
+        Returns:
+            Dictionary of settings with sensitive values masked.
+        """
+        return {
+            "database_url": self._redact_url(self.database.url),
+            "redis_url": self._redact_url(self.redis.url),
+            "polygon": {
+                "rpc_url": self.polygon.rpc_url,
+                "fallback_rpc_url": self.polygon.fallback_rpc_url or "(not set)",
+            },
+            "polymarket": {
+                "ws_url": self.polymarket.ws_url,
+                "api_key": "(set)" if self.polymarket.api_key else "(not set)",
+            },
+            "discord_enabled": str(self.discord.enabled),
+            "telegram_enabled": str(self.telegram.enabled),
+            "log_level": self.log_level,
+            "health_port": str(self.health_port),
+            "dry_run": str(self.dry_run),
+        }
+
+    @staticmethod
+    def _redact_url(url: str) -> str:
+        """Redact password from URL if present."""
+        if "@" in url and "://" in url:
+            # URL has credentials - redact the password
+            protocol_end = url.index("://") + 3
+            at_pos = url.index("@")
+            creds_part = url[protocol_end:at_pos]
+            if ":" in creds_part:
+                username = creds_part.split(":")[0]
+                return f"{url[:protocol_end]}{username}:***@{url[at_pos + 1 :]}"
+        return url
+
+
+@lru_cache(maxsize=1)
+def get_settings() -> Settings:
+    """Get the application settings singleton.
+
+    Uses LRU cache to ensure settings are loaded only once and
+    reused across the application.
+
+    Returns:
+        The Settings instance.
+
+    Raises:
+        ValidationError: If required environment variables are missing
+            or have invalid values.
+    """
+    return Settings()
+
+
+def clear_settings_cache() -> None:
+    """Clear the settings cache.
+
+    Useful for testing when you need to reload settings with
+    different environment variables.
+    """
+    get_settings.cache_clear()

src/polymarket_insider_tracker/detector/scorer.py

@@ -268,7 +268,7 @@ class RiskScorer:
         """
         key = f"{self._key_prefix}{wallet_address}:{market_id}"
         deleted = await self._redis.delete(key)
-        return deleted > 0
+        return int(deleted) > 0
 
     async def assess_batch(self, bundles: list[SignalBundle]) -> list[RiskAssessment]:
         """Assess multiple trade bundles.

src/polymarket_insider_tracker/ingestor/clob_client.py

@@ -287,7 +287,8 @@ class ClobClient:
 
         try:
             response = self._client.get_midpoint(token_id)
-            return response.get("mid")
+            mid = response.get("mid")
+            return str(mid) if mid is not None else None
         except Exception as e:
             logger.warning("Failed to get midpoint for %s: %s", token_id, e)
             return None
@@ -307,7 +308,8 @@ class ClobClient:
 
         try:
             response = self._client.get_price(token_id, side=side)
-            return response.get("price")
+            price = response.get("price")
+            return str(price) if price is not None else None
         except Exception as e:
             logger.warning("Failed to get %s price for %s: %s", side, token_id, e)
             return None
@@ -321,7 +323,7 @@ class ClobClient:
         try:
             self._rate_limiter.acquire_sync()
             result = self._client.get_ok()
-            return result == "OK"
+            return str(result) == "OK"
         except Exception as e:
             logger.error("Health check failed: %s", e)
             return False
@@ -334,7 +336,8 @@ class ClobClient:
         """
         try:
             self._rate_limiter.acquire_sync()
-            return self._client.get_server_time()
+            result = self._client.get_server_time()
+            return int(result) if result is not None else None
         except Exception as e:
             logger.error("Failed to get server time: %s", e)
             return None

src/polymarket_insider_tracker/ingestor/metadata_sync.py

@@ -11,7 +11,7 @@ import logging
 from collections.abc import Callable
 from dataclasses import dataclass
 from datetime import UTC, datetime
-from enum import Enum
+from enum import StrEnum
 
 from redis.asyncio import Redis
 
@@ -27,7 +27,7 @@ DEFAULT_CACHE_TTL_SECONDS = 600  # 10 minutes
 DEFAULT_REDIS_KEY_PREFIX = "polymarket:market:"
 
 
-class SyncState(str, Enum):
+class SyncState(StrEnum):
     """State of the metadata synchronizer."""
 
     STOPPED = "stopped"
@@ -351,7 +351,7 @@ class MarketMetadataSync:
         """
         key = f"{self._key_prefix}{condition_id}"
         deleted = await self._redis.delete(key)
-        return deleted > 0
+        return int(deleted) > 0
 
     async def force_sync(self) -> None:
         """Force an immediate sync of all markets.

src/polymarket_insider_tracker/ingestor/publisher.py

@@ -186,9 +186,10 @@ class EventPublisher:
             The entry ID assigned by Redis.
         """
         data = _serialize_trade_event(event)
+        # redis-py typing expects broader dict type than dict[str, str]
         entry_id = await self._redis.xadd(
             self._stream_name,
-            data,
+            data,  # type: ignore[arg-type]
             maxlen=self._max_len,
         )
         # entry_id may be bytes or str
@@ -213,7 +214,8 @@ class EventPublisher:
         pipe = self._redis.pipeline()
         for event in events:
             data = _serialize_trade_event(event)
-            pipe.xadd(self._stream_name, data, maxlen=self._max_len)
+            # redis-py typing expects broader dict type than dict[str, str]
+            pipe.xadd(self._stream_name, data, maxlen=self._max_len)  # type: ignore[arg-type]
 
         results = await pipe.execute()
 
@@ -384,7 +386,8 @@ class EventPublisher:
         """
         if not entry_ids:
             return 0
-        return await self._redis.xack(self._stream_name, group_name, *entry_ids)
+        result = await self._redis.xack(self._stream_name, group_name, *entry_ids)
+        return int(result)
 
     async def get_stream_info(self) -> dict[str, Any]:
         """Get information about the stream.
@@ -404,7 +407,8 @@ class EventPublisher:
         Returns:
             Number of entries in the stream.
         """
-        return await self._redis.xlen(self._stream_name)
+        result = await self._redis.xlen(self._stream_name)
+        return int(result)
 
     async def trim_stream(self, max_len: int | None = None) -> int:
         """Trim the stream to a maximum length.
@@ -416,4 +420,5 @@ class EventPublisher:
             Number of entries removed.
         """
         length = max_len or self._max_len
-        return await self._redis.xtrim(self._stream_name, maxlen=length)
+        result = await self._redis.xtrim(self._stream_name, maxlen=length)
+        return int(result)

src/polymarket_insider_tracker/pipeline.py

@@ -0,0 +1,480 @@
+"""Main pipeline orchestrator for Polymarket Insider Tracker.
+
+This module provides the Pipeline class that wires together all detection
+components and manages the event flow from ingestion to alerting.
+"""
+
+from __future__ import annotations
+
+import asyncio
+import contextlib
+import logging
+from dataclasses import dataclass
+from datetime import UTC, datetime
+from enum import StrEnum
+from typing import TYPE_CHECKING
+
+from redis.asyncio import Redis
+
+from polymarket_insider_tracker.alerter.channels.discord import DiscordChannel
+from polymarket_insider_tracker.alerter.channels.telegram import TelegramChannel
+from polymarket_insider_tracker.alerter.dispatcher import AlertChannel, AlertDispatcher
+from polymarket_insider_tracker.alerter.formatter import AlertFormatter
+from polymarket_insider_tracker.config import Settings, get_settings
+from polymarket_insider_tracker.detector.fresh_wallet import FreshWalletDetector
+from polymarket_insider_tracker.detector.scorer import RiskScorer, SignalBundle
+from polymarket_insider_tracker.detector.size_anomaly import SizeAnomalyDetector
+from polymarket_insider_tracker.ingestor.clob_client import ClobClient
+from polymarket_insider_tracker.ingestor.metadata_sync import MarketMetadataSync
+from polymarket_insider_tracker.ingestor.websocket import TradeStreamHandler
+from polymarket_insider_tracker.profiler.analyzer import WalletAnalyzer
+from polymarket_insider_tracker.profiler.chain import PolygonClient
+from polymarket_insider_tracker.storage.database import DatabaseManager
+
+if TYPE_CHECKING:
+    from typing import Any
+
+    from polymarket_insider_tracker.detector.models import (
+        FreshWalletSignal,
+        SizeAnomalySignal,
+    )
+    from polymarket_insider_tracker.ingestor.models import TradeEvent
+
+logger = logging.getLogger(__name__)
+
+
+class PipelineState(StrEnum):
+    """Pipeline lifecycle states."""
+
+    STOPPED = "stopped"
+    STARTING = "starting"
+    RUNNING = "running"
+    STOPPING = "stopping"
+    ERROR = "error"
+
+
+@dataclass
+class PipelineStats:
+    """Statistics for the pipeline."""
+
+    started_at: datetime | None = None
+    trades_processed: int = 0
+    signals_generated: int = 0
+    alerts_sent: int = 0
+    errors: int = 0
+    last_trade_time: datetime | None = None
+    last_error: str | None = None
+
+
+class Pipeline:
+    """Main pipeline orchestrator for the Polymarket Insider Tracker.
+
+    This class wires together all detection components and manages the
+    event flow from trade ingestion through profiling, detection, and alerting.
+
+    Pipeline flow:
+        WebSocket Trade Stream → Wallet Profiler → Detectors → Risk Scorer → Alerter
+
+    Example:
+        ```python
+        from polymarket_insider_tracker.config import get_settings
+        from polymarket_insider_tracker.pipeline import Pipeline
+
+        settings = get_settings()
+        pipeline = Pipeline(settings)
+
+        await pipeline.start()
+        # Pipeline runs until stop() is called
+        await pipeline.stop()
+        ```
+    """
+
+    def __init__(
+        self,
+        settings: Settings | None = None,
+        *,
+        dry_run: bool | None = None,
+    ) -> None:
+        """Initialize the pipeline.
+
+        Args:
+            settings: Application settings. If not provided, uses get_settings().
+            dry_run: If True, skip sending alerts. Overrides settings.dry_run.
+        """
+        self._settings = settings or get_settings()
+        self._dry_run = dry_run if dry_run is not None else self._settings.dry_run
+
+        self._state = PipelineState.STOPPED
+        self._stats = PipelineStats()
+
+        # Components (initialized in start())
+        self._redis: Redis | None = None
+        self._db_manager: DatabaseManager | None = None
+        self._polygon_client: PolygonClient | None = None
+        self._clob_client: ClobClient | None = None
+        self._metadata_sync: MarketMetadataSync | None = None
+        self._wallet_analyzer: WalletAnalyzer | None = None
+        self._fresh_wallet_detector: FreshWalletDetector | None = None
+        self._size_anomaly_detector: SizeAnomalyDetector | None = None
+        self._risk_scorer: RiskScorer | None = None
+        self._alert_formatter: AlertFormatter | None = None
+        self._alert_dispatcher: AlertDispatcher | None = None
+        self._trade_stream: TradeStreamHandler | None = None
+
+        # Synchronization
+        self._stop_event: asyncio.Event | None = None
+        self._stream_task: asyncio.Task[None] | None = None
+
+    @property
+    def state(self) -> PipelineState:
+        """Current pipeline state."""
+        return self._state
+
+    @property
+    def stats(self) -> PipelineStats:
+        """Current pipeline statistics."""
+        return self._stats
+
+    @property
+    def is_running(self) -> bool:
+        """Check if pipeline is running."""
+        return self._state == PipelineState.RUNNING
+
+    async def start(self) -> None:
+        """Start the pipeline.
+
+        Initializes all components and begins processing trades.
+
+        Raises:
+            RuntimeError: If pipeline is already running.
+            Exception: If any component fails to initialize.
+        """
+        if self._state != PipelineState.STOPPED:
+            raise RuntimeError(f"Cannot start pipeline in state {self._state}")
+
+        self._state = PipelineState.STARTING
+        self._stop_event = asyncio.Event()
+        logger.info("Starting pipeline...")
+
+        try:
+            await self._initialize_components()
+            await self._start_background_services()
+            self._stats.started_at = datetime.now(UTC)
+            self._state = PipelineState.RUNNING
+            logger.info("Pipeline started successfully")
+        except Exception as e:
+            self._state = PipelineState.ERROR
+            self._stats.last_error = str(e)
+            logger.error("Failed to start pipeline: %s", e)
+            await self._cleanup()
+            raise
+
+    async def stop(self) -> None:
+        """Stop the pipeline gracefully.
+
+        Stops all background services and cleans up resources.
+        """
+        if self._state == PipelineState.STOPPED:
+            return
+
+        self._state = PipelineState.STOPPING
+        logger.info("Stopping pipeline...")
+
+        if self._stop_event:
+            self._stop_event.set()
+
+        await self._stop_background_services()
+        await self._cleanup()
+
+        self._state = PipelineState.STOPPED
+        logger.info("Pipeline stopped")
+
+    async def _initialize_components(self) -> None:
+        """Initialize all pipeline components."""
+        settings = self._settings
+
+        # Initialize Redis
+        logger.debug("Initializing Redis connection...")
+        self._redis = Redis.from_url(settings.redis.url)
+
+        # Initialize Database Manager
+        logger.debug("Initializing database manager...")
+        self._db_manager = DatabaseManager(
+            settings.database.url,
+            async_mode=True,
+        )
+
+        # Initialize Polygon client
+        logger.debug("Initializing Polygon client...")
+        self._polygon_client = PolygonClient(
+            settings.polygon.rpc_url,
+            fallback_rpc_url=settings.polygon.fallback_rpc_url,
+            redis=self._redis,
+        )
+
+        # Initialize CLOB client
+        logger.debug("Initializing CLOB client...")
+        api_key = (
+            settings.polymarket.api_key.get_secret_value() if settings.polymarket.api_key else None
+        )
+        self._clob_client = ClobClient(api_key=api_key)
+
+        # Initialize Market Metadata Sync
+        logger.debug("Initializing market metadata sync...")
+        self._metadata_sync = MarketMetadataSync(
+            redis=self._redis,
+            clob_client=self._clob_client,
+        )
+
+        # Initialize Wallet Analyzer
+        logger.debug("Initializing wallet analyzer...")
+        self._wallet_analyzer = WalletAnalyzer(
+            self._polygon_client,
+            redis=self._redis,
+        )
+
+        # Initialize Detectors
+        logger.debug("Initializing detectors...")
+        self._fresh_wallet_detector = FreshWalletDetector(self._wallet_analyzer)
+        self._size_anomaly_detector = SizeAnomalyDetector(self._metadata_sync)
+
+        # Initialize Risk Scorer
+        logger.debug("Initializing risk scorer...")
+        self._risk_scorer = RiskScorer(self._redis)
+
+        # Initialize Alerting
+        logger.debug("Initializing alerting components...")
+        self._alert_formatter = AlertFormatter(verbosity="detailed")
+        channels = self._build_alert_channels()
+        self._alert_dispatcher = AlertDispatcher(channels)
+
+        # Initialize Trade Stream
+        logger.debug("Initializing trade stream handler...")
+        self._trade_stream = TradeStreamHandler(
+            on_trade=self._on_trade,
+            host=settings.polymarket.ws_url,
+        )
+
+        logger.info("All components initialized")
+
+    def _build_alert_channels(self) -> list[AlertChannel]:
+        """Build list of enabled alert channels."""
+        channels: list[AlertChannel] = []
+        settings = self._settings
+
+        if settings.discord.enabled and settings.discord.webhook_url:
+            webhook_url = settings.discord.webhook_url.get_secret_value()
+            channels.append(DiscordChannel(webhook_url))
+            logger.info("Discord channel enabled")
+
+        if settings.telegram.enabled:
+            bot_token = settings.telegram.bot_token
+            chat_id = settings.telegram.chat_id
+            if bot_token and chat_id:
+                channels.append(
+                    TelegramChannel(
+                        bot_token.get_secret_value(),
+                        chat_id,
+                    )
+                )
+                logger.info("Telegram channel enabled")
+
+        if not channels:
+            logger.warning("No alert channels configured")
+
+        return channels
+
+    async def _start_background_services(self) -> None:
+        """Start background services."""
+        # Start metadata sync
+        if self._metadata_sync:
+            logger.debug("Starting metadata sync service...")
+            await self._metadata_sync.start()
+
+        # Start trade stream in background task
+        if self._trade_stream:
+            logger.debug("Starting trade stream...")
+            self._stream_task = asyncio.create_task(self._run_trade_stream())
+
+    async def _run_trade_stream(self) -> None:
+        """Run the trade stream in a task."""
+        if not self._trade_stream:
+            return
+
+        try:
+            await self._trade_stream.start()
+        except asyncio.CancelledError:
+            logger.debug("Trade stream task cancelled")
+        except Exception as e:
+            logger.error("Trade stream error: %s", e)
+            self._stats.last_error = str(e)
+            self._stats.errors += 1
+
+    async def _stop_background_services(self) -> None:
+        """Stop background services."""
+        # Stop trade stream
+        if self._trade_stream:
+            logger.debug("Stopping trade stream...")
+            await self._trade_stream.stop()
+
+        # Cancel stream task
+        if self._stream_task:
+            self._stream_task.cancel()
+            with contextlib.suppress(asyncio.CancelledError):
+                await self._stream_task
+            self._stream_task = None
+
+        # Stop metadata sync
+        if self._metadata_sync:
+            logger.debug("Stopping metadata sync...")
+            await self._metadata_sync.stop()
+
+    async def _cleanup(self) -> None:
+        """Clean up resources."""
+        # Close database connections
+        if self._db_manager:
+            await self._db_manager.dispose_async()
+            self._db_manager = None
+
+        # Close Redis connection
+        if self._redis:
+            await self._redis.aclose()
+            self._redis = None
+
+        logger.debug("Resources cleaned up")
+
+    async def _on_trade(self, trade: TradeEvent) -> None:
+        """Process a single trade event.
+
+        This is the main event handler that runs the detection pipeline:
+        1. Run fresh wallet detection
+        2. Run size anomaly detection
+        3. Score the combined signals
+        4. Send alert if threshold exceeded
+
+        Args:
+            trade: The trade event from the WebSocket stream.
+        """
+        self._stats.trades_processed += 1
+        self._stats.last_trade_time = datetime.now(UTC)
+
+        try:
+            # Run detectors in parallel
+            fresh_signal, size_signal = await asyncio.gather(
+                self._detect_fresh_wallet(trade),
+                self._detect_size_anomaly(trade),
+            )
+
+            # Bundle signals
+            bundle = SignalBundle(
+                trade_event=trade,
+                fresh_wallet_signal=fresh_signal,
+                size_anomaly_signal=size_signal,
+            )
+
+            # Score and potentially alert
+            if fresh_signal or size_signal:
+                self._stats.signals_generated += 1
+                await self._score_and_alert(bundle)
+
+        except Exception as e:
+            logger.error("Error processing trade %s: %s", trade.trade_id, e)
+            self._stats.errors += 1
+            self._stats.last_error = str(e)
+
+    async def _detect_fresh_wallet(self, trade: TradeEvent) -> FreshWalletSignal | None:
+        """Run fresh wallet detection."""
+        if not self._fresh_wallet_detector:
+            return None
+        try:
+            return await self._fresh_wallet_detector.analyze(trade)
+        except Exception as e:
+            logger.warning("Fresh wallet detection failed for %s: %s", trade.trade_id, e)
+            return None
+
+    async def _detect_size_anomaly(self, trade: TradeEvent) -> SizeAnomalySignal | None:
+        """Run size anomaly detection."""
+        if not self._size_anomaly_detector:
+            return None
+        try:
+            return await self._size_anomaly_detector.analyze(trade)
+        except Exception as e:
+            logger.warning("Size anomaly detection failed for %s: %s", trade.trade_id, e)
+            return None
+
+    async def _score_and_alert(self, bundle: SignalBundle) -> None:
+        """Score signals and send alert if threshold exceeded."""
+        if not self._risk_scorer or not self._alert_formatter or not self._alert_dispatcher:
+            return
+
+        # Get risk assessment
+        assessment = await self._risk_scorer.assess(bundle)
+
+        if not assessment.should_alert:
+            logger.debug(
+                "Trade %s below alert threshold (score=%.2f)",
+                bundle.trade_event.trade_id,
+                assessment.weighted_score,
+            )
+            return
+
+        # Format and dispatch alert
+        formatted_alert = self._alert_formatter.format(assessment)
+
+        if self._dry_run:
+            logger.info(
+                "[DRY RUN] Would send alert: wallet=%s, score=%.2f",
+                assessment.wallet_address[:10] + "...",
+                assessment.weighted_score,
+            )
+            return
+
+        result = await self._alert_dispatcher.dispatch(formatted_alert)
+
+        if result.all_succeeded:
+            self._stats.alerts_sent += 1
+            logger.info(
+                "Alert sent successfully: wallet=%s, score=%.2f",
+                assessment.wallet_address[:10] + "...",
+                assessment.weighted_score,
+            )
+        else:
+            logger.warning(
+                "Alert partially failed: %d/%d channels succeeded",
+                result.success_count,
+                result.success_count + result.failure_count,
+            )
+
+    async def run(self) -> None:
+        """Start the pipeline and run until interrupted.
+
+        This is a convenience method that starts the pipeline and
+        blocks until a stop signal is received.
+
+        Example:
+            ```python
+            pipeline = Pipeline()
+            try:
+                await pipeline.run()
+            except KeyboardInterrupt:
+                pass
+            ```
+        """
+        await self.start()
+
+        try:
+            if self._stop_event:
+                await self._stop_event.wait()
+        except asyncio.CancelledError:
+            pass
+        finally:
+            await self.stop()
+
+    async def __aenter__(self) -> Pipeline:
+        """Async context manager entry."""
+        await self.start()
+        return self
+
+    async def __aexit__(self, *args: Any) -> None:
+        """Async context manager exit."""
+        await self.stop()

src/polymarket_insider_tracker/profiler/funding.py

@@ -232,6 +232,7 @@ class FundingTracer:
         )
 
         # Get logs with Transfer event filtering by recipient
+        # Note: web3 typing is overly restrictive for block params
         logs = await w3.eth.get_logs(
             {
                 "address": AsyncWeb3.to_checksum_address(token_address),
@@ -240,8 +241,8 @@ class FundingTracer:
                     None,  # from (any)
                     padded_to,  # to (target address)
                 ],
-                "fromBlock": from_block,
+                "fromBlock": from_block,  # type: ignore[typeddict-item]
-                "toBlock": to_block,
+                "toBlock": to_block,  # type: ignore[typeddict-item]
             }
         )
 
@@ -317,7 +318,7 @@ class FundingTracer:
                     origin_type="error",
                 )
             else:
-                chains[addr.lower()] = result  # type: ignore[assignment]
+                chains[addr.lower()] = result
 
         return chains
 

src/polymarket_insider_tracker/shutdown.py

@@ -0,0 +1,325 @@
+"""Graceful shutdown handler for Polymarket Insider Tracker.
+
+This module provides signal handling and graceful shutdown coordination
+for the async pipeline components.
+
+Usage:
+    ```python
+    async def main():
+        shutdown = GracefulShutdown()
+
+        async with shutdown:
+            pipeline = Pipeline(settings)
+            await pipeline.start()
+
+            # Wait for shutdown signal
+            await shutdown.wait()
+
+            # Graceful cleanup
+            await pipeline.stop()
+    ```
+"""
+
+from __future__ import annotations
+
+import asyncio
+import logging
+import signal
+import sys
+from collections.abc import Callable
+from contextlib import suppress
+from types import FrameType
+from typing import TYPE_CHECKING
+
+if TYPE_CHECKING:
+    from typing import Any
+
+logger = logging.getLogger(__name__)
+
+# Default shutdown timeout in seconds
+DEFAULT_SHUTDOWN_TIMEOUT = 30.0
+
+# Signals to trap for graceful shutdown
+SHUTDOWN_SIGNALS = (signal.SIGTERM, signal.SIGINT)
+
+
+class ShutdownTimeoutError(Exception):
+    """Raised when graceful shutdown exceeds timeout."""
+
+
+class GracefulShutdown:
+    """Graceful shutdown handler with signal trapping.
+
+    This class provides coordinated shutdown handling for async applications.
+    It traps SIGTERM and SIGINT signals and provides an async event that
+    can be awaited to detect shutdown requests.
+
+    Features:
+        - SIGTERM and SIGINT signal trapping
+        - Async event-based shutdown coordination
+        - Configurable shutdown timeout
+        - Async context manager support
+        - Cleanup callback registration
+        - Force exit on second signal or timeout
+
+    Example:
+        ```python
+        shutdown = GracefulShutdown(timeout=30.0)
+
+        async with shutdown:
+            await some_long_running_task()
+            # Automatically handles cleanup on signals
+        ```
+    """
+
+    def __init__(
+        self,
+        timeout: float = DEFAULT_SHUTDOWN_TIMEOUT,
+        *,
+        exit_on_timeout: bool = True,
+    ) -> None:
+        """Initialize the shutdown handler.
+
+        Args:
+            timeout: Maximum time in seconds to wait for graceful shutdown.
+            exit_on_timeout: If True, force exit when timeout is exceeded.
+        """
+        self._timeout = timeout
+        self._exit_on_timeout = exit_on_timeout
+
+        self._shutdown_event: asyncio.Event | None = None
+        self._shutdown_requested = False
+        self._force_exit_requested = False
+        self._original_handlers: dict[signal.Signals, Any] = {}
+        self._cleanup_callbacks: list[Callable[[], Any]] = []
+        self._loop: asyncio.AbstractEventLoop | None = None
+
+    @property
+    def timeout(self) -> float:
+        """Shutdown timeout in seconds."""
+        return self._timeout
+
+    @property
+    def is_shutdown_requested(self) -> bool:
+        """Check if shutdown has been requested."""
+        return self._shutdown_requested
+
+    @property
+    def is_force_exit_requested(self) -> bool:
+        """Check if force exit has been requested (second signal received)."""
+        return self._force_exit_requested
+
+    def register_cleanup(self, callback: Callable[[], Any]) -> None:
+        """Register a cleanup callback to run during shutdown.
+
+        Args:
+            callback: A callable (sync or async) to run during shutdown.
+        """
+        self._cleanup_callbacks.append(callback)
+
+    def request_shutdown(self) -> None:
+        """Programmatically request shutdown.
+
+        This can be used to trigger shutdown from application code
+        instead of waiting for a signal.
+        """
+        if not self._shutdown_requested:
+            self._shutdown_requested = True
+            logger.info("Shutdown requested programmatically")
+            if self._shutdown_event:
+                self._shutdown_event.set()
+
+    async def wait(self) -> None:
+        """Wait for a shutdown signal.
+
+        This coroutine blocks until a shutdown signal is received
+        or request_shutdown() is called.
+        """
+        if self._shutdown_event is None:
+            self._shutdown_event = asyncio.Event()
+
+        await self._shutdown_event.wait()
+
+    async def wait_with_timeout(self) -> bool:
+        """Wait for shutdown with timeout.
+
+        Returns:
+            True if shutdown was requested, False if timeout occurred.
+        """
+        if self._shutdown_event is None:
+            self._shutdown_event = asyncio.Event()
+
+        try:
+            await asyncio.wait_for(
+                self._shutdown_event.wait(),
+                timeout=self._timeout,
+            )
+            return True
+        except TimeoutError:
+            return False
+
+    def install_signal_handlers(self) -> None:
+        """Install signal handlers for graceful shutdown.
+
+        Traps SIGTERM and SIGINT to trigger graceful shutdown.
+        On Windows, only SIGINT is trapped as SIGTERM is not available.
+        """
+        self._loop = asyncio.get_running_loop()
+        self._shutdown_event = asyncio.Event()
+
+        # Platform-specific signal handling
+        if sys.platform == "win32":
+            # Windows: use signal.signal for SIGINT only
+            self._install_windows_handlers()
+        else:
+            # Unix: use loop.add_signal_handler for both signals
+            self._install_unix_handlers()
+
+        logger.debug("Signal handlers installed")
+
+    def _install_unix_handlers(self) -> None:
+        """Install Unix signal handlers using the event loop."""
+        if self._loop is None:
+            return
+
+        for sig in SHUTDOWN_SIGNALS:
+            try:
+                self._loop.add_signal_handler(
+                    sig,
+                    self._handle_signal,
+                    sig,
+                )
+                logger.debug("Installed handler for %s", sig.name)
+            except (ValueError, OSError) as e:
+                logger.warning("Could not install handler for %s: %s", sig.name, e)
+
+    def _install_windows_handlers(self) -> None:
+        """Install Windows signal handlers using signal.signal."""
+        for sig in SHUTDOWN_SIGNALS:
+            try:
+                self._original_handlers[sig] = signal.signal(
+                    sig,
+                    self._handle_signal_sync,
+                )
+                logger.debug("Installed handler for %s", sig.name)
+            except (ValueError, OSError) as e:
+                logger.warning("Could not install handler for %s: %s", sig.name, e)
+
+    def remove_signal_handlers(self) -> None:
+        """Remove installed signal handlers and restore originals."""
+        if sys.platform == "win32":
+            self._remove_windows_handlers()
+        else:
+            self._remove_unix_handlers()
+
+        logger.debug("Signal handlers removed")
+
+    def _remove_unix_handlers(self) -> None:
+        """Remove Unix signal handlers."""
+        if self._loop is None:
+            return
+
+        for sig in SHUTDOWN_SIGNALS:
+            with suppress(ValueError, OSError):
+                self._loop.remove_signal_handler(sig)
+
+    def _remove_windows_handlers(self) -> None:
+        """Remove Windows signal handlers and restore originals."""
+        for sig, original in self._original_handlers.items():
+            with suppress(ValueError, OSError):
+                signal.signal(sig, original)
+        self._original_handlers.clear()
+
+    def _handle_signal(self, sig: signal.Signals) -> None:
+        """Handle shutdown signal (Unix version).
+
+        Args:
+            sig: The signal that was received.
+        """
+        if self._shutdown_requested:
+            # Second signal - force exit
+            self._force_exit_requested = True
+            logger.warning("Received %s again - forcing exit!", sig.name)
+            sys.exit(128 + sig.value)
+        else:
+            self._shutdown_requested = True
+            logger.info("Received %s - initiating graceful shutdown...", sig.name)
+            if self._shutdown_event:
+                self._shutdown_event.set()
+
+    def _handle_signal_sync(self, sig: int, _frame: FrameType | None) -> None:
+        """Handle shutdown signal (Windows version).
+
+        Args:
+            sig: The signal number that was received.
+            _frame: The current stack frame (unused).
+        """
+        sig_enum = signal.Signals(sig)
+        self._handle_signal(sig_enum)
+
+    async def run_cleanup_callbacks(self) -> None:
+        """Run all registered cleanup callbacks."""
+        for callback in self._cleanup_callbacks:
+            try:
+                result = callback()
+                if asyncio.iscoroutine(result):
+                    await result
+            except Exception as e:
+                logger.error("Cleanup callback failed: %s", e)
+
+    async def __aenter__(self) -> GracefulShutdown:
+        """Async context manager entry - install signal handlers."""
+        self.install_signal_handlers()
+        return self
+
+    async def __aexit__(self, *_args: Any) -> None:
+        """Async context manager exit - cleanup."""
+        self.remove_signal_handlers()
+        await self.run_cleanup_callbacks()
+
+
+async def run_with_graceful_shutdown(
+    coro: Any,
+    *,
+    timeout: float = DEFAULT_SHUTDOWN_TIMEOUT,
+) -> None:
+    """Run an async coroutine with graceful shutdown handling.
+
+    This is a convenience function that wraps a coroutine with
+    signal handling and timeout-based cleanup.
+
+    Args:
+        coro: The coroutine to run.
+        timeout: Maximum time to wait for graceful shutdown.
+
+    Example:
+        ```python
+        async def my_app():
+            await asyncio.sleep(3600)  # Run for an hour
+
+        # Will handle SIGTERM/SIGINT gracefully
+        await run_with_graceful_shutdown(my_app())
+        ```
+    """
+    shutdown = GracefulShutdown(timeout=timeout)
+
+    async with shutdown:
+        task = asyncio.create_task(coro)
+
+        # Wait for either task completion or shutdown signal
+        shutdown_wait = asyncio.create_task(shutdown.wait())
+
+        done, pending = await asyncio.wait(
+            [task, shutdown_wait],
+            return_when=asyncio.FIRST_COMPLETED,
+        )
+
+        # Cancel pending tasks
+        for pending_task in pending:
+            pending_task.cancel()
+            with suppress(asyncio.CancelledError):
+                await pending_task
+
+        # If the main task is in done, get any exception
+        if task in done:
+            task.result()

src/polymarket_insider_tracker/storage/repos.py

@@ -208,20 +208,20 @@ class WalletRepository:
             await self.session.execute(stmt)
         except Exception:
             # Fall back to SQLite upsert for testing
-            stmt = sqlite_insert(WalletProfileModel).values(**values, created_at=now)
+            sqlite_stmt = sqlite_insert(WalletProfileModel).values(**values, created_at=now)
-            stmt = stmt.on_conflict_do_update(
+            sqlite_stmt = sqlite_stmt.on_conflict_do_update(
                 index_elements=["address"],
                 set_={
-                    "nonce": stmt.excluded.nonce,
+                    "nonce": sqlite_stmt.excluded.nonce,
-                    "first_seen_at": stmt.excluded.first_seen_at,
+                    "first_seen_at": sqlite_stmt.excluded.first_seen_at,
-                    "is_fresh": stmt.excluded.is_fresh,
+                    "is_fresh": sqlite_stmt.excluded.is_fresh,
-                    "matic_balance": stmt.excluded.matic_balance,
+                    "matic_balance": sqlite_stmt.excluded.matic_balance,
-                    "usdc_balance": stmt.excluded.usdc_balance,
+                    "usdc_balance": sqlite_stmt.excluded.usdc_balance,
-                    "analyzed_at": stmt.excluded.analyzed_at,
+                    "analyzed_at": sqlite_stmt.excluded.analyzed_at,
-                    "updated_at": stmt.excluded.updated_at,
+                    "updated_at": sqlite_stmt.excluded.updated_at,
                 },
             )
-            await self.session.execute(stmt)
+            await self.session.execute(sqlite_stmt)
 
         await self.session.flush()
         return dto
@@ -238,7 +238,8 @@ class WalletRepository:
         result = await self.session.execute(
             delete(WalletProfileModel).where(WalletProfileModel.address == address.lower())
         )
-        return result.rowcount > 0
+        # SQLAlchemy Result does have rowcount but typing doesn't reflect it
+        return (result.rowcount or 0) > 0  # type: ignore[attr-defined]
 
     async def mark_stale(self, address: str) -> bool:
         """Mark a wallet profile as stale (soft delete).
@@ -257,7 +258,8 @@ class WalletRepository:
             .where(WalletProfileModel.address == address.lower())
             .values(analyzed_at=stale_time, updated_at=datetime.now(UTC))
         )
-        return result.rowcount > 0
+        # SQLAlchemy Result does have rowcount but typing doesn't reflect it
+        return (result.rowcount or 0) > 0  # type: ignore[attr-defined]
 
 
 class FundingRepository:
@@ -478,12 +480,12 @@ class RelationshipRepository:
             await self.session.execute(stmt)
         except Exception:
             # Fall back to SQLite upsert for testing
-            stmt = sqlite_insert(WalletRelationshipModel).values(**values)
+            sqlite_stmt = sqlite_insert(WalletRelationshipModel).values(**values)
-            stmt = stmt.on_conflict_do_update(
+            sqlite_stmt = sqlite_stmt.on_conflict_do_update(
                 index_elements=["wallet_a", "wallet_b", "relationship_type"],
-                set_={"confidence": stmt.excluded.confidence},
+                set_={"confidence": sqlite_stmt.excluded.confidence},
             )
-            await self.session.execute(stmt)
+            await self.session.execute(sqlite_stmt)
 
         await self.session.flush()
         return dto
@@ -506,4 +508,5 @@ class RelationshipRepository:
                 WalletRelationshipModel.relationship_type == relationship_type,
             )
         )
-        return result.rowcount > 0
+        # SQLAlchemy Result does have rowcount but typing doesn't reflect it
+        return (result.rowcount or 0) > 0  # type: ignore[attr-defined]

tests/ingestor/test_clob_client.py

@@ -7,7 +7,6 @@ import pytest
 
 from polymarket_insider_tracker.ingestor.clob_client import (
     ClobClient,
-    ClobClientError,
     RateLimiter,
     RetryError,
     with_retry,
@@ -253,17 +252,23 @@ class TestClobClient:
         assert market.condition_id == "0xabc"
         assert len(market.tokens) == 2
 
-    @pytest.mark.xfail(reason="Retry logic wraps exception differently - see #49")
     def test_get_market_not_found(self, mock_base_client: MagicMock) -> None:
-        """Test error handling when market not found."""
+        """Test error handling when market not found.
+
+        When the underlying API call fails, the @with_retry decorator will
+        retry the operation. After all retries are exhausted, it raises
+        RetryError wrapping the original exception.
+        """
         mock_base_client.get_market.side_effect = Exception("Not found")
 
         client = ClobClient()
 
-        with pytest.raises(ClobClientError) as exc_info:
+        with pytest.raises(RetryError) as exc_info:
             client.get_market("0xnotfound")
 
-        assert "0xnotfound" in str(exc_info.value)
+        # The RetryError wraps the original exception
+        assert "get_market" in str(exc_info.value)
+        assert exc_info.value.last_exception is not None
 
     def test_get_orderbook(self, mock_base_client: MagicMock) -> None:
         """Test fetching an orderbook."""

tests/ingestor/test_websocket.py

@@ -3,7 +3,7 @@
 import asyncio
 import json
 from decimal import Decimal
-from unittest.mock import AsyncMock, MagicMock, patch
+from unittest.mock import AsyncMock, patch
 
 import pytest
 
@@ -275,7 +275,6 @@ class TestTradeStreamHandlerIntegration:
     """
 
     @pytest.mark.asyncio
-    @pytest.mark.xfail(reason="Async mock iterator signature issue - see #49")
     async def test_start_and_receive_trades(self) -> None:
         """Test starting handler and receiving trades."""
         received_trades: list[TradeEvent] = []
@@ -288,11 +287,6 @@ class TestTradeStreamHandlerIntegration:
             initial_reconnect_delay=0.01,
         )
 
-        # Create mock WebSocket that sends one trade then closes
-        mock_ws = MagicMock()
-        mock_ws.send = AsyncMock()
-        mock_ws.close = AsyncMock()
-
         trade_message = json.dumps(
             {
                 "topic": "activity",
@@ -311,12 +305,33 @@ class TestTradeStreamHandlerIntegration:
             }
         )
 
-        # Mock async iteration
+        # Create a proper async iterable mock WebSocket
-        async def mock_iter() -> None:
+        class MockWebSocket:
-            yield trade_message
+            """Mock WebSocket that yields one message then stops."""
-            await handler.stop()  # Stop after first message
 
-        mock_ws.__aiter__ = mock_iter
+            def __init__(self, handler: TradeStreamHandler, message: str):
+                self.handler = handler
+                self.message = message
+                self.sent = False
+
+            async def send(self, _msg: str) -> None:
+                pass
+
+            async def close(self) -> None:
+                pass
+
+            def __aiter__(self):
+                return self
+
+            async def __anext__(self) -> str:
+                if not self.sent:
+                    self.sent = True
+                    return self.message
+                # Stop the handler and raise StopAsyncIteration
+                await self.handler.stop()
+                raise StopAsyncIteration
+
+        mock_ws = MockWebSocket(handler, trade_message)
 
         with patch("websockets.connect", AsyncMock(return_value=mock_ws)):
             # Run with timeout to prevent hanging

tests/test_config.py

@@ -0,0 +1,329 @@
+"""Tests for configuration management service."""
+
+from __future__ import annotations
+
+import os
+from typing import TYPE_CHECKING
+from unittest.mock import patch
+
+import pytest
+from pydantic import ValidationError
+
+from polymarket_insider_tracker.config import (
+    DatabaseSettings,
+    DiscordSettings,
+    PolygonSettings,
+    PolymarketSettings,
+    RedisSettings,
+    Settings,
+    TelegramSettings,
+    clear_settings_cache,
+    get_settings,
+)
+
+if TYPE_CHECKING:
+    from collections.abc import Iterator
+
+
+@pytest.fixture(autouse=True)
+def clear_cache() -> Iterator[None]:
+    """Clear settings cache before and after each test."""
+    clear_settings_cache()
+    yield
+    clear_settings_cache()
+
+
+class TestDatabaseSettings:
+    """Tests for DatabaseSettings."""
+
+    def test_valid_postgresql_url(self) -> None:
+        """Test valid PostgreSQL URL."""
+        with patch.dict(os.environ, {"DATABASE_URL": "postgresql://user:pass@localhost/db"}):
+            settings = DatabaseSettings()
+            assert settings.url == "postgresql://user:pass@localhost/db"
+
+    def test_valid_asyncpg_url(self) -> None:
+        """Test valid asyncpg URL."""
+        with patch.dict(
+            os.environ, {"DATABASE_URL": "postgresql+asyncpg://user:pass@localhost/db"}
+        ):
+            settings = DatabaseSettings()
+            assert settings.url == "postgresql+asyncpg://user:pass@localhost/db"
+
+    def test_invalid_url_raises(self) -> None:
+        """Test that invalid database URL raises validation error."""
+        with (
+            patch.dict(os.environ, {"DATABASE_URL": "mysql://user:pass@localhost/db"}),
+            pytest.raises(ValidationError, match="PostgreSQL connection string"),
+        ):
+            DatabaseSettings()
+
+
+class TestRedisSettings:
+    """Tests for RedisSettings."""
+
+    def test_default_url(self) -> None:
+        """Test default Redis URL."""
+        with patch.dict(os.environ, {}, clear=True):
+            settings = RedisSettings()
+            assert settings.url == "redis://localhost:6379"
+
+    def test_custom_url(self) -> None:
+        """Test custom Redis URL."""
+        with patch.dict(os.environ, {"REDIS_URL": "redis://redis:6380"}):
+            settings = RedisSettings()
+            assert settings.url == "redis://redis:6380"
+
+    def test_invalid_url_raises(self) -> None:
+        """Test that invalid Redis URL raises validation error."""
+        with (
+            patch.dict(os.environ, {"REDIS_URL": "http://localhost:6379"}),
+            pytest.raises(ValidationError, match="redis://"),
+        ):
+            RedisSettings()
+
+
+class TestPolygonSettings:
+    """Tests for PolygonSettings."""
+
+    def test_default_rpc_url(self) -> None:
+        """Test default Polygon RPC URL."""
+        with patch.dict(os.environ, {}, clear=True):
+            settings = PolygonSettings()
+            assert settings.rpc_url == "https://polygon-rpc.com"
+            assert settings.fallback_rpc_url is None
+
+    def test_custom_urls(self) -> None:
+        """Test custom Polygon RPC URLs."""
+        with patch.dict(
+            os.environ,
+            {
+                "POLYGON_RPC_URL": "https://alchemy.io/polygon",
+                "POLYGON_FALLBACK_RPC_URL": "https://backup.polygon.io",
+            },
+        ):
+            settings = PolygonSettings()
+            assert settings.rpc_url == "https://alchemy.io/polygon"
+            assert settings.fallback_rpc_url == "https://backup.polygon.io"
+
+    def test_invalid_url_raises(self) -> None:
+        """Test that invalid RPC URL raises validation error."""
+        with (
+            patch.dict(os.environ, {"POLYGON_RPC_URL": "ws://polygon.io"}),
+            pytest.raises(ValidationError, match="HTTP"),
+        ):
+            PolygonSettings()
+
+
+class TestPolymarketSettings:
+    """Tests for PolymarketSettings."""
+
+    def test_default_ws_url(self) -> None:
+        """Test default Polymarket WebSocket URL."""
+        with patch.dict(os.environ, {}, clear=True):
+            settings = PolymarketSettings()
+            assert "polymarket.com" in settings.ws_url
+            assert settings.api_key is None
+
+    def test_custom_api_key(self) -> None:
+        """Test custom API key (secret)."""
+        with patch.dict(os.environ, {"POLYMARKET_API_KEY": "secret-key-123"}):
+            settings = PolymarketSettings()
+            assert settings.api_key is not None
+            assert settings.api_key.get_secret_value() == "secret-key-123"
+
+    def test_invalid_ws_url_raises(self) -> None:
+        """Test that invalid WebSocket URL raises validation error."""
+        with (
+            patch.dict(os.environ, {"POLYMARKET_WS_URL": "http://polymarket.com"}),
+            pytest.raises(ValidationError, match="ws://"),
+        ):
+            PolymarketSettings()
+
+
+class TestDiscordSettings:
+    """Tests for DiscordSettings."""
+
+    def test_disabled_by_default(self) -> None:
+        """Test Discord is disabled when no webhook URL."""
+        with patch.dict(os.environ, {}, clear=True):
+            settings = DiscordSettings()
+            assert not settings.enabled
+            assert settings.webhook_url is None
+
+    def test_enabled_with_webhook(self) -> None:
+        """Test Discord is enabled with webhook URL."""
+        with patch.dict(os.environ, {"DISCORD_WEBHOOK_URL": "https://discord.com/webhook/123"}):
+            settings = DiscordSettings()
+            assert settings.enabled
+            assert settings.webhook_url is not None
+
+
+class TestTelegramSettings:
+    """Tests for TelegramSettings."""
+
+    def test_disabled_by_default(self) -> None:
+        """Test Telegram is disabled when no credentials."""
+        with patch.dict(os.environ, {}, clear=True):
+            settings = TelegramSettings()
+            assert not settings.enabled
+
+    def test_disabled_with_partial_config(self) -> None:
+        """Test Telegram is disabled with only token or chat_id."""
+        with patch.dict(os.environ, {"TELEGRAM_BOT_TOKEN": "token123"}):
+            settings = TelegramSettings()
+            assert not settings.enabled
+
+        with patch.dict(os.environ, {"TELEGRAM_CHAT_ID": "12345"}):
+            settings = TelegramSettings()
+            assert not settings.enabled
+
+    def test_enabled_with_full_config(self) -> None:
+        """Test Telegram is enabled with both token and chat_id."""
+        with patch.dict(
+            os.environ,
+            {
+                "TELEGRAM_BOT_TOKEN": "token123",
+                "TELEGRAM_CHAT_ID": "12345",
+            },
+        ):
+            settings = TelegramSettings()
+            assert settings.enabled
+
+
+class TestSettings:
+    """Tests for main Settings class."""
+
+    def test_loads_with_required_vars(self) -> None:
+        """Test settings load with required environment variables."""
+        with patch.dict(
+            os.environ,
+            {
+                "DATABASE_URL": "postgresql://user:pass@localhost/db",
+                "REDIS_URL": "redis://localhost:6379",
+            },
+        ):
+            settings = Settings()
+            assert settings.database.url == "postgresql://user:pass@localhost/db"
+            assert settings.redis.url == "redis://localhost:6379"
+
+    def test_default_log_level(self) -> None:
+        """Test default log level is INFO."""
+        with patch.dict(
+            os.environ,
+            {"DATABASE_URL": "postgresql://user:pass@localhost/db"},
+        ):
+            settings = Settings()
+            assert settings.log_level == "INFO"
+
+    def test_custom_log_level(self) -> None:
+        """Test custom log level."""
+        with patch.dict(
+            os.environ,
+            {
+                "DATABASE_URL": "postgresql://user:pass@localhost/db",
+                "LOG_LEVEL": "DEBUG",
+            },
+        ):
+            settings = Settings()
+            assert settings.log_level == "DEBUG"
+
+    def test_invalid_log_level_raises(self) -> None:
+        """Test invalid log level raises validation error."""
+        with (
+            patch.dict(
+                os.environ,
+                {
+                    "DATABASE_URL": "postgresql://user:pass@localhost/db",
+                    "LOG_LEVEL": "TRACE",
+                },
+            ),
+            pytest.raises(ValidationError),
+        ):
+            Settings()
+
+    def test_health_port_validation(self) -> None:
+        """Test health port must be valid port number."""
+        with (
+            patch.dict(
+                os.environ,
+                {
+                    "DATABASE_URL": "postgresql://user:pass@localhost/db",
+                    "HEALTH_PORT": "99999",
+                },
+            ),
+            pytest.raises(ValidationError, match="65535"),
+        ):
+            Settings()
+
+    def test_get_logging_level(self) -> None:
+        """Test get_logging_level returns numeric level."""
+        import logging
+
+        with patch.dict(
+            os.environ,
+            {
+                "DATABASE_URL": "postgresql://user:pass@localhost/db",
+                "LOG_LEVEL": "WARNING",
+            },
+        ):
+            settings = Settings()
+            assert settings.get_logging_level() == logging.WARNING
+
+    def test_redacted_summary(self) -> None:
+        """Test redacted_summary masks sensitive data."""
+        with patch.dict(
+            os.environ,
+            {
+                "DATABASE_URL": "postgresql://user:secretpass@localhost/db",
+                "REDIS_URL": "redis://localhost:6379",
+            },
+        ):
+            settings = Settings()
+            summary = settings.redacted_summary()
+
+            # Database password should be redacted
+            db_url = summary["database_url"]
+            assert isinstance(db_url, str)
+            assert "secretpass" not in db_url
+            assert "***" in db_url
+            assert "user" in db_url
+
+
+class TestGetSettings:
+    """Tests for get_settings singleton."""
+
+    def test_returns_same_instance(self) -> None:
+        """Test get_settings returns cached instance."""
+        with patch.dict(
+            os.environ,
+            {"DATABASE_URL": "postgresql://user:pass@localhost/db"},
+        ):
+            settings1 = get_settings()
+            settings2 = get_settings()
+            assert settings1 is settings2
+
+    def test_clear_cache_allows_reload(self) -> None:
+        """Test clear_settings_cache allows reloading settings."""
+        with patch.dict(
+            os.environ,
+            {
+                "DATABASE_URL": "postgresql://user:pass@localhost/db",
+                "LOG_LEVEL": "INFO",
+            },
+        ):
+            settings1 = get_settings()
+            assert settings1.log_level == "INFO"
+
+        clear_settings_cache()
+
+        with patch.dict(
+            os.environ,
+            {
+                "DATABASE_URL": "postgresql://user:pass@localhost/db",
+                "LOG_LEVEL": "DEBUG",
+            },
+        ):
+            settings2 = get_settings()
+            assert settings2.log_level == "DEBUG"
+            assert settings1 is not settings2

tests/test_main.py

@@ -0,0 +1,214 @@
+"""Tests for the CLI entry point."""
+
+from __future__ import annotations
+
+from unittest.mock import patch
+
+import pytest
+
+from polymarket_insider_tracker.__main__ import (
+    EXIT_CONFIG_ERROR,
+    EXIT_SUCCESS,
+    configure_logging,
+    create_parser,
+    main,
+    print_banner,
+    run_config_check,
+    validate_config,
+)
+
+
+class TestCreateParser:
+    """Tests for argument parser creation."""
+
+    def test_parser_has_version(self):
+        """Parser should have version flag."""
+        parser = create_parser()
+        with pytest.raises(SystemExit) as exc_info:
+            parser.parse_args(["--version"])
+        assert exc_info.value.code == 0
+
+    def test_parser_config_check(self):
+        """Parser should accept --config-check flag."""
+        parser = create_parser()
+        args = parser.parse_args(["--config-check"])
+        assert args.config_check is True
+
+    def test_parser_log_level(self):
+        """Parser should accept --log-level option."""
+        parser = create_parser()
+        args = parser.parse_args(["--log-level", "DEBUG"])
+        assert args.log_level == "DEBUG"
+
+    def test_parser_dry_run(self):
+        """Parser should accept --dry-run flag."""
+        parser = create_parser()
+        args = parser.parse_args(["--dry-run"])
+        assert args.dry_run is True
+
+    def test_parser_health_port(self):
+        """Parser should accept --health-port option."""
+        parser = create_parser()
+        args = parser.parse_args(["--health-port", "9090"])
+        assert args.health_port == 9090
+
+    def test_parser_default_values(self):
+        """Parser should have correct defaults."""
+        parser = create_parser()
+        args = parser.parse_args([])
+        assert args.config_check is False
+        assert args.log_level is None
+        assert args.dry_run is False
+        assert args.health_port is None
+
+
+class TestConfigureLogging:
+    """Tests for logging configuration."""
+
+    def test_configure_logging_info(self):
+        """Should configure logging at INFO level."""
+        configure_logging("INFO")
+        import logging
+
+        assert logging.getLogger().level == logging.INFO
+
+    def test_configure_logging_debug(self):
+        """Should configure logging at DEBUG level."""
+        configure_logging("DEBUG")
+        import logging
+
+        assert logging.getLogger().level == logging.DEBUG
+
+
+class TestPrintBanner:
+    """Tests for banner printing."""
+
+    def test_banner_contains_app_name(self, capsys):
+        """Banner should contain application name."""
+        print_banner()
+        captured = capsys.readouterr()
+        assert "Polymarket Insider Tracker" in captured.out
+
+    def test_banner_contains_version(self, capsys):
+        """Banner should contain version."""
+        print_banner()
+        captured = capsys.readouterr()
+        assert "v0.1.0" in captured.out
+
+
+class TestValidateConfig:
+    """Tests for configuration validation."""
+
+    def test_validate_config_success(self, monkeypatch):
+        """Should return settings on valid config."""
+        monkeypatch.setenv("DATABASE_URL", "postgresql://localhost/test")
+
+        settings = validate_config()
+        assert settings is not None
+
+    def test_validate_config_failure(self, monkeypatch, capsys):
+        """Should return None on invalid config."""
+        # Clear any existing DATABASE_URL
+        monkeypatch.delenv("DATABASE_URL", raising=False)
+
+        settings = validate_config()
+        assert settings is None
+
+        captured = capsys.readouterr()
+        assert "Configuration validation failed" in captured.err
+
+
+class TestRunConfigCheck:
+    """Tests for config check mode."""
+
+    def test_config_check_prints_summary(self, monkeypatch, capsys):
+        """Config check should print configuration summary."""
+        monkeypatch.setenv("DATABASE_URL", "postgresql://localhost/test")
+
+        settings = validate_config()
+        assert settings is not None
+
+        result = run_config_check(settings)
+        assert result == EXIT_SUCCESS
+
+        captured = capsys.readouterr()
+        assert "Configuration is valid!" in captured.out
+        assert "Configuration:" in captured.out
+
+
+class TestMain:
+    """Tests for main entry point."""
+
+    def test_main_with_config_check(self, monkeypatch):
+        """Main should exit successfully with --config-check."""
+        monkeypatch.setenv("DATABASE_URL", "postgresql://localhost/test")
+
+        with pytest.raises(SystemExit) as exc_info:
+            main(["--config-check"])
+
+        assert exc_info.value.code == EXIT_SUCCESS
+
+    def test_main_with_invalid_config(self, monkeypatch):
+        """Main should exit with config error on invalid config."""
+        monkeypatch.delenv("DATABASE_URL", raising=False)
+
+        with pytest.raises(SystemExit) as exc_info:
+            main([])
+
+        assert exc_info.value.code == EXIT_CONFIG_ERROR
+
+    def test_main_with_dry_run_and_config_check(self, monkeypatch):
+        """Main should handle dry-run with config-check."""
+        monkeypatch.setenv("DATABASE_URL", "postgresql://localhost/test")
+
+        with pytest.raises(SystemExit) as exc_info:
+            main(["--config-check", "--dry-run"])
+
+        assert exc_info.value.code == EXIT_SUCCESS
+
+    @patch("polymarket_insider_tracker.__main__.run_pipeline")
+    @patch("polymarket_insider_tracker.__main__.asyncio.run")
+    def test_main_runs_pipeline(self, mock_asyncio_run, _mock_run_pipeline, monkeypatch):
+        """Main should run pipeline when not in config-check mode."""
+        monkeypatch.setenv("DATABASE_URL", "postgresql://localhost/test")
+        mock_asyncio_run.return_value = EXIT_SUCCESS
+
+        with pytest.raises(SystemExit) as exc_info:
+            main([])
+
+        assert exc_info.value.code == EXIT_SUCCESS
+        mock_asyncio_run.assert_called_once()
+
+
+class TestIntegration:
+    """Integration tests for CLI invocation."""
+
+    def test_cli_help_option(self, capsys):
+        """CLI should display help with -h option."""
+        with pytest.raises(SystemExit) as exc_info:
+            main(["-h"])
+
+        assert exc_info.value.code == 0
+        captured = capsys.readouterr()
+        assert "polymarket-insider-tracker" in captured.out
+        assert "--config-check" in captured.out
+        assert "--dry-run" in captured.out
+        assert "--log-level" in captured.out
+
+    def test_cli_version_option(self, capsys):
+        """CLI should display version with --version option."""
+        with pytest.raises(SystemExit) as exc_info:
+            main(["--version"])
+
+        assert exc_info.value.code == 0
+        captured = capsys.readouterr()
+        assert "0.1.0" in captured.out
+
+    def test_cli_invalid_log_level(self, capsys):
+        """CLI should reject invalid log level."""
+        with pytest.raises(SystemExit) as exc_info:
+            main(["--log-level", "INVALID"])
+
+        assert exc_info.value.code != 0
+        captured = capsys.readouterr()
+        assert "invalid choice" in captured.err

tests/test_pipeline.py

@@ -0,0 +1,394 @@
+"""Tests for the main pipeline orchestrator."""
+
+from __future__ import annotations
+
+import asyncio
+from datetime import UTC, datetime
+from decimal import Decimal
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+
+from polymarket_insider_tracker.config import Settings
+from polymarket_insider_tracker.detector.models import FreshWalletSignal
+from polymarket_insider_tracker.detector.scorer import SignalBundle
+from polymarket_insider_tracker.ingestor.models import TradeEvent
+from polymarket_insider_tracker.pipeline import Pipeline, PipelineState
+from polymarket_insider_tracker.profiler.models import WalletProfile
+
+
+@pytest.fixture
+def mock_settings():
+    """Create mock settings for testing."""
+    # Create nested mock objects
+    redis = MagicMock()
+    redis.url = "redis://localhost:6379"
+
+    database = MagicMock()
+    database.url = "postgresql+asyncpg://user:pass@localhost/db"
+
+    polygon = MagicMock()
+    polygon.rpc_url = "https://polygon-rpc.com"
+    polygon.fallback_rpc_url = None
+
+    polymarket = MagicMock()
+    polymarket.ws_url = "wss://ws-subscriptions-clob.polymarket.com/ws/market"
+    polymarket.api_key = None
+
+    discord = MagicMock()
+    discord.enabled = False
+    discord.webhook_url = None
+
+    telegram = MagicMock()
+    telegram.enabled = False
+    telegram.bot_token = None
+    telegram.chat_id = None
+
+    settings = MagicMock(spec=Settings)
+    settings.redis = redis
+    settings.database = database
+    settings.polygon = polygon
+    settings.polymarket = polymarket
+    settings.discord = discord
+    settings.telegram = telegram
+    settings.dry_run = True
+    return settings
+
+
+@pytest.fixture
+def sample_trade_event():
+    """Create a sample trade event for testing."""
+    return TradeEvent(
+        trade_id="0x" + "a" * 64,
+        wallet_address="0x" + "b" * 40,
+        market_id="0x" + "c" * 64,
+        asset_id="asset_123",
+        side="BUY",
+        price=Decimal("0.65"),
+        size=Decimal("5000"),
+        timestamp=datetime.now(UTC),
+        outcome="Yes",
+        outcome_index=0,
+        event_title="Test Market",
+        market_slug="test-market",
+    )
+
+
+@pytest.fixture
+def sample_wallet_profile():
+    """Create a sample wallet profile for testing."""
+    return WalletProfile(
+        address="0x" + "b" * 40,
+        nonce=2,
+        first_seen=datetime.now(UTC),
+        age_hours=1.5,
+        is_fresh=True,
+        total_tx_count=2,
+        matic_balance=Decimal("100"),
+        usdc_balance=Decimal("5000"),
+        fresh_threshold=5,
+    )
+
+
+class TestPipelineState:
+    """Tests for pipeline state management."""
+
+    def test_initial_state_is_stopped(self, mock_settings):
+        """Pipeline should start in stopped state."""
+        pipeline = Pipeline(mock_settings)
+        assert pipeline.state == PipelineState.STOPPED
+
+    def test_is_running_property(self, mock_settings):
+        """is_running property should reflect state."""
+        pipeline = Pipeline(mock_settings)
+        assert not pipeline.is_running
+
+        pipeline._state = PipelineState.RUNNING
+        assert pipeline.is_running
+
+
+class TestPipelineStats:
+    """Tests for pipeline statistics."""
+
+    def test_initial_stats(self, mock_settings):
+        """Pipeline should have zero stats initially."""
+        pipeline = Pipeline(mock_settings)
+        stats = pipeline.stats
+
+        assert stats.started_at is None
+        assert stats.trades_processed == 0
+        assert stats.signals_generated == 0
+        assert stats.alerts_sent == 0
+        assert stats.errors == 0
+
+
+class TestPipelineInitialization:
+    """Tests for pipeline initialization."""
+
+    def test_dry_run_from_settings(self, mock_settings):
+        """Pipeline should use dry_run from settings by default."""
+        mock_settings.dry_run = True
+        pipeline = Pipeline(mock_settings)
+        assert pipeline._dry_run is True
+
+        mock_settings.dry_run = False
+        pipeline = Pipeline(mock_settings)
+        assert pipeline._dry_run is False
+
+    def test_dry_run_override(self, mock_settings):
+        """Pipeline should allow overriding dry_run."""
+        mock_settings.dry_run = False
+        pipeline = Pipeline(mock_settings, dry_run=True)
+        assert pipeline._dry_run is True
+
+    def test_uses_get_settings_when_none_provided(self):
+        """Pipeline should call get_settings if no settings provided."""
+        with patch("polymarket_insider_tracker.pipeline.get_settings") as mock_get:
+            mock_get.return_value = MagicMock(spec=Settings)
+            mock_get.return_value.dry_run = False
+            Pipeline()
+            mock_get.assert_called_once()
+
+
+class TestBuildAlertChannels:
+    """Tests for alert channel building."""
+
+    def test_no_channels_when_none_enabled(self, mock_settings):
+        """Should return empty list when no channels enabled."""
+        mock_settings.discord.enabled = False
+        mock_settings.telegram.enabled = False
+
+        pipeline = Pipeline(mock_settings)
+        channels = pipeline._build_alert_channels()
+
+        assert channels == []
+
+    def test_discord_channel_when_enabled(self, mock_settings):
+        """Should add Discord channel when enabled."""
+        mock_settings.discord.enabled = True
+        mock_settings.discord.webhook_url = MagicMock()
+        mock_settings.discord.webhook_url.get_secret_value.return_value = (
+            "https://discord.com/webhook"
+        )
+
+        pipeline = Pipeline(mock_settings)
+        channels = pipeline._build_alert_channels()
+
+        assert len(channels) == 1
+        assert channels[0].name == "discord"
+
+    def test_telegram_channel_when_enabled(self, mock_settings):
+        """Should add Telegram channel when enabled."""
+        mock_settings.telegram.enabled = True
+        mock_settings.telegram.bot_token = MagicMock()
+        mock_settings.telegram.bot_token.get_secret_value.return_value = "bot_token"
+        mock_settings.telegram.chat_id = "chat_123"
+
+        pipeline = Pipeline(mock_settings)
+        channels = pipeline._build_alert_channels()
+
+        assert len(channels) == 1
+        assert channels[0].name == "telegram"
+
+    def test_both_channels_when_both_enabled(self, mock_settings):
+        """Should add both channels when both enabled."""
+        mock_settings.discord.enabled = True
+        mock_settings.discord.webhook_url = MagicMock()
+        mock_settings.discord.webhook_url.get_secret_value.return_value = (
+            "https://discord.com/webhook"
+        )
+        mock_settings.telegram.enabled = True
+        mock_settings.telegram.bot_token = MagicMock()
+        mock_settings.telegram.bot_token.get_secret_value.return_value = "bot_token"
+        mock_settings.telegram.chat_id = "chat_123"
+
+        pipeline = Pipeline(mock_settings)
+        channels = pipeline._build_alert_channels()
+
+        assert len(channels) == 2
+
+
+class TestOnTrade:
+    """Tests for trade event processing."""
+
+    @pytest.mark.asyncio
+    async def test_on_trade_increments_stats(self, mock_settings, sample_trade_event):
+        """Processing a trade should increment stats."""
+        pipeline = Pipeline(mock_settings)
+        pipeline._fresh_wallet_detector = AsyncMock(return_value=None)
+        pipeline._size_anomaly_detector = AsyncMock(return_value=None)
+
+        await pipeline._on_trade(sample_trade_event)
+
+        assert pipeline.stats.trades_processed == 1
+        assert pipeline.stats.last_trade_time is not None
+
+    @pytest.mark.asyncio
+    async def test_on_trade_runs_detectors_in_parallel(self, mock_settings, sample_trade_event):
+        """Detectors should run in parallel."""
+        pipeline = Pipeline(mock_settings)
+        pipeline._fresh_wallet_detector = AsyncMock()
+        pipeline._size_anomaly_detector = AsyncMock()
+
+        # Make detectors take some time
+        async def slow_detect(*_args):
+            await asyncio.sleep(0.1)
+            return None
+
+        pipeline._fresh_wallet_detector.analyze = slow_detect
+        pipeline._size_anomaly_detector.analyze = slow_detect
+
+        start = asyncio.get_event_loop().time()
+        await pipeline._on_trade(sample_trade_event)
+        elapsed = asyncio.get_event_loop().time() - start
+
+        # Should complete in ~0.1s not ~0.2s
+        assert elapsed < 0.15
+
+    @pytest.mark.asyncio
+    async def test_on_trade_handles_detector_errors(self, mock_settings, sample_trade_event):
+        """Should handle detector errors gracefully."""
+        pipeline = Pipeline(mock_settings)
+        pipeline._fresh_wallet_detector = MagicMock()
+        pipeline._fresh_wallet_detector.analyze = AsyncMock(side_effect=Exception("Detector error"))
+        pipeline._size_anomaly_detector = MagicMock()
+        pipeline._size_anomaly_detector.analyze = AsyncMock(return_value=None)
+
+        # Should not raise
+        await pipeline._on_trade(sample_trade_event)
+
+        # Should still increment trades processed
+        assert pipeline.stats.trades_processed == 1
+
+    @pytest.mark.asyncio
+    async def test_on_trade_calls_score_and_alert_when_signals(
+        self, mock_settings, sample_trade_event, sample_wallet_profile
+    ):
+        """Should call score_and_alert when signals are detected."""
+        pipeline = Pipeline(mock_settings)
+
+        # Create a signal
+        fresh_signal = FreshWalletSignal(
+            trade_event=sample_trade_event,
+            wallet_profile=sample_wallet_profile,
+            confidence=0.8,
+            factors={"base": 0.5, "brand_new": 0.2},
+        )
+
+        pipeline._fresh_wallet_detector = MagicMock()
+        pipeline._fresh_wallet_detector.analyze = AsyncMock(return_value=fresh_signal)
+        pipeline._size_anomaly_detector = MagicMock()
+        pipeline._size_anomaly_detector.analyze = AsyncMock(return_value=None)
+
+        # Mock score_and_alert
+        pipeline._score_and_alert = AsyncMock()
+
+        await pipeline._on_trade(sample_trade_event)
+
+        # Should call score_and_alert with the bundle
+        pipeline._score_and_alert.assert_called_once()
+        bundle = pipeline._score_and_alert.call_args[0][0]
+        assert bundle.fresh_wallet_signal == fresh_signal
+        assert pipeline.stats.signals_generated == 1
+
+
+class TestScoreAndAlert:
+    """Tests for scoring and alerting."""
+
+    @pytest.mark.asyncio
+    async def test_dry_run_skips_dispatch(
+        self, mock_settings, sample_trade_event, sample_wallet_profile
+    ):
+        """Dry run should skip actual alert dispatch."""
+        mock_settings.dry_run = True
+        pipeline = Pipeline(mock_settings)
+
+        # Create mock components
+        pipeline._risk_scorer = MagicMock()
+        pipeline._risk_scorer.assess = AsyncMock(
+            return_value=MagicMock(
+                should_alert=True,
+                wallet_address="0x" + "b" * 40,
+                weighted_score=0.85,
+            )
+        )
+        pipeline._alert_formatter = MagicMock()
+        pipeline._alert_dispatcher = MagicMock()
+        pipeline._alert_dispatcher.dispatch = AsyncMock()
+
+        bundle = SignalBundle(
+            trade_event=sample_trade_event,
+            fresh_wallet_signal=FreshWalletSignal(
+                trade_event=sample_trade_event,
+                wallet_profile=sample_wallet_profile,
+                confidence=0.8,
+                factors={},
+            ),
+        )
+
+        await pipeline._score_and_alert(bundle)
+
+        # Dispatcher should NOT be called in dry run
+        pipeline._alert_dispatcher.dispatch.assert_not_called()
+
+    @pytest.mark.asyncio
+    async def test_no_alert_when_below_threshold(self, mock_settings, sample_trade_event):
+        """Should not alert when below threshold."""
+        pipeline = Pipeline(mock_settings)
+
+        # Create mock components
+        pipeline._risk_scorer = MagicMock()
+        pipeline._risk_scorer.assess = AsyncMock(
+            return_value=MagicMock(
+                should_alert=False,
+                weighted_score=0.4,
+            )
+        )
+        pipeline._alert_formatter = MagicMock()
+        pipeline._alert_dispatcher = MagicMock()
+
+        bundle = SignalBundle(trade_event=sample_trade_event)
+
+        await pipeline._score_and_alert(bundle)
+
+        # Formatter should NOT be called
+        pipeline._alert_formatter.format.assert_not_called()
+
+
+class TestPipelineLifecycle:
+    """Tests for pipeline lifecycle methods."""
+
+    @pytest.mark.asyncio
+    async def test_cannot_start_when_not_stopped(self, mock_settings):
+        """Should raise error when starting non-stopped pipeline."""
+        pipeline = Pipeline(mock_settings)
+        pipeline._state = PipelineState.RUNNING
+
+        with pytest.raises(RuntimeError, match="Cannot start pipeline"):
+            await pipeline.start()
+
+    @pytest.mark.asyncio
+    async def test_stop_when_already_stopped(self, mock_settings):
+        """Stop should be no-op when already stopped."""
+        pipeline = Pipeline(mock_settings)
+        assert pipeline.state == PipelineState.STOPPED
+
+        # Should not raise
+        await pipeline.stop()
+        assert pipeline.state == PipelineState.STOPPED
+
+
+class TestPipelineContextManager:
+    """Tests for async context manager."""
+
+    @pytest.mark.asyncio
+    async def test_context_manager_calls_start_and_stop(self, mock_settings):
+        """Context manager should call start and stop."""
+        pipeline = Pipeline(mock_settings)
+        pipeline.start = AsyncMock()
+        pipeline.stop = AsyncMock()
+
+        async with pipeline:
+            pipeline.start.assert_called_once()
+
+        pipeline.stop.assert_called_once()

tests/test_shutdown.py

@@ -0,0 +1,319 @@
+"""Tests for the graceful shutdown handler."""
+
+from __future__ import annotations
+
+import asyncio
+import signal
+import sys
+from unittest.mock import MagicMock, patch
+
+import pytest
+
+from polymarket_insider_tracker.shutdown import (
+    DEFAULT_SHUTDOWN_TIMEOUT,
+    SHUTDOWN_SIGNALS,
+    GracefulShutdown,
+    run_with_graceful_shutdown,
+)
+
+
+class TestGracefulShutdownInit:
+    """Tests for GracefulShutdown initialization."""
+
+    def test_default_timeout(self) -> None:
+        """Should use default timeout when not specified."""
+        shutdown = GracefulShutdown()
+        assert shutdown.timeout == DEFAULT_SHUTDOWN_TIMEOUT
+
+    def test_custom_timeout(self) -> None:
+        """Should accept custom timeout."""
+        shutdown = GracefulShutdown(timeout=60.0)
+        assert shutdown.timeout == 60.0
+
+    def test_initial_state(self) -> None:
+        """Should start in non-shutdown state."""
+        shutdown = GracefulShutdown()
+        assert shutdown.is_shutdown_requested is False
+        assert shutdown.is_force_exit_requested is False
+
+
+class TestRequestShutdown:
+    """Tests for programmatic shutdown requests."""
+
+    async def test_request_shutdown_sets_flag(self) -> None:
+        """Should set shutdown requested flag."""
+        shutdown = GracefulShutdown()
+        shutdown.request_shutdown()
+        assert shutdown.is_shutdown_requested is True
+
+    async def test_request_shutdown_sets_event(self) -> None:
+        """Should set the shutdown event when called."""
+        shutdown = GracefulShutdown()
+        shutdown._shutdown_event = asyncio.Event()
+
+        shutdown.request_shutdown()
+
+        assert shutdown._shutdown_event.is_set()
+
+    async def test_request_shutdown_idempotent(self) -> None:
+        """Multiple requests should be idempotent."""
+        shutdown = GracefulShutdown()
+        shutdown._shutdown_event = asyncio.Event()
+
+        shutdown.request_shutdown()
+        shutdown.request_shutdown()
+        shutdown.request_shutdown()
+
+        assert shutdown.is_shutdown_requested is True
+
+
+class TestWait:
+    """Tests for waiting for shutdown."""
+
+    async def test_wait_blocks_until_shutdown(self) -> None:
+        """Wait should block until shutdown is requested."""
+        shutdown = GracefulShutdown()
+
+        async def request_after_delay() -> None:
+            await asyncio.sleep(0.1)
+            shutdown.request_shutdown()
+
+        asyncio.create_task(request_after_delay())
+
+        # Should complete after the delay
+        await asyncio.wait_for(shutdown.wait(), timeout=1.0)
+
+        assert shutdown.is_shutdown_requested is True
+
+    async def test_wait_with_timeout_returns_true_on_shutdown(self) -> None:
+        """wait_with_timeout should return True when shutdown is requested."""
+        shutdown = GracefulShutdown(timeout=1.0)
+
+        async def request_after_delay() -> None:
+            await asyncio.sleep(0.05)
+            shutdown.request_shutdown()
+
+        asyncio.create_task(request_after_delay())
+
+        result = await shutdown.wait_with_timeout()
+        assert result is True
+
+    async def test_wait_with_timeout_returns_false_on_timeout(self) -> None:
+        """wait_with_timeout should return False when timeout occurs."""
+        shutdown = GracefulShutdown(timeout=0.05)
+
+        # Don't request shutdown, let it timeout
+        result = await shutdown.wait_with_timeout()
+        assert result is False
+
+
+class TestSignalHandlers:
+    """Tests for signal handler installation and removal."""
+
+    async def test_install_signal_handlers_creates_event(self) -> None:
+        """Installing handlers should create the shutdown event."""
+        shutdown = GracefulShutdown()
+        shutdown.install_signal_handlers()
+
+        try:
+            assert shutdown._shutdown_event is not None
+            assert not shutdown._shutdown_event.is_set()
+        finally:
+            shutdown.remove_signal_handlers()
+
+    @pytest.mark.skipif(sys.platform == "win32", reason="Unix-specific test")
+    async def test_unix_signal_handler_installed(self) -> None:
+        """On Unix, should install loop signal handlers."""
+        shutdown = GracefulShutdown()
+
+        with patch.object(asyncio.get_running_loop(), "add_signal_handler") as mock_add:
+            shutdown.install_signal_handlers()
+
+            # Should have been called for both SIGTERM and SIGINT
+            assert mock_add.call_count >= 1
+
+        shutdown.remove_signal_handlers()
+
+    @pytest.mark.skipif(sys.platform != "win32", reason="Windows-specific test")
+    async def test_windows_signal_handler_installed(self) -> None:
+        """On Windows, should install signal.signal handlers."""
+        shutdown = GracefulShutdown()
+
+        with patch("signal.signal") as mock_signal:
+            shutdown.install_signal_handlers()
+
+            # Should have been called for available signals
+            assert mock_signal.call_count >= 1
+
+        shutdown.remove_signal_handlers()
+
+
+class TestHandleSignal:
+    """Tests for signal handling behavior."""
+
+    async def test_first_signal_sets_shutdown_event(self) -> None:
+        """First signal should set the shutdown event."""
+        shutdown = GracefulShutdown()
+        shutdown._shutdown_event = asyncio.Event()
+
+        shutdown._handle_signal(signal.SIGTERM)
+
+        assert shutdown.is_shutdown_requested is True
+        assert shutdown._shutdown_event.is_set()
+        assert shutdown.is_force_exit_requested is False
+
+    async def test_second_signal_force_exits(self) -> None:
+        """Second signal should trigger force exit."""
+        shutdown = GracefulShutdown()
+        shutdown._shutdown_event = asyncio.Event()
+        shutdown._shutdown_requested = True  # First signal already received
+
+        with pytest.raises(SystemExit) as exc_info:
+            shutdown._handle_signal(signal.SIGTERM)
+
+        assert exc_info.value.code == 128 + signal.SIGTERM.value
+        assert shutdown.is_force_exit_requested is True
+
+
+class TestCleanupCallbacks:
+    """Tests for cleanup callback registration and execution."""
+
+    async def test_register_sync_callback(self) -> None:
+        """Should register sync cleanup callbacks."""
+        shutdown = GracefulShutdown()
+        callback = MagicMock()
+
+        shutdown.register_cleanup(callback)
+
+        assert callback in shutdown._cleanup_callbacks
+
+    async def test_run_sync_cleanup_callback(self) -> None:
+        """Should run sync cleanup callbacks."""
+        shutdown = GracefulShutdown()
+        callback = MagicMock()
+        shutdown.register_cleanup(callback)
+
+        await shutdown.run_cleanup_callbacks()
+
+        callback.assert_called_once()
+
+    async def test_run_async_cleanup_callback(self) -> None:
+        """Should run async cleanup callbacks."""
+        shutdown = GracefulShutdown()
+        called = False
+
+        async def async_callback() -> None:
+            nonlocal called
+            called = True
+
+        shutdown.register_cleanup(async_callback)
+
+        await shutdown.run_cleanup_callbacks()
+
+        assert called is True
+
+    async def test_cleanup_callback_error_logged(self) -> None:
+        """Cleanup callback errors should be logged, not raised."""
+        shutdown = GracefulShutdown()
+
+        def failing_callback() -> None:
+            raise ValueError("Cleanup failed")
+
+        shutdown.register_cleanup(failing_callback)
+
+        # Should not raise
+        await shutdown.run_cleanup_callbacks()
+
+
+class TestAsyncContextManager:
+    """Tests for async context manager protocol."""
+
+    async def test_context_manager_installs_handlers(self) -> None:
+        """Entering context should install signal handlers."""
+        shutdown = GracefulShutdown()
+
+        async with shutdown:
+            assert shutdown._shutdown_event is not None
+            assert shutdown._loop is not None
+
+    async def test_context_manager_removes_handlers(self) -> None:
+        """Exiting context should remove signal handlers."""
+        shutdown = GracefulShutdown()
+
+        with patch.object(shutdown, "remove_signal_handlers") as mock_remove:
+            async with shutdown:
+                pass
+
+            mock_remove.assert_called_once()
+
+    async def test_context_manager_runs_cleanup(self) -> None:
+        """Exiting context should run cleanup callbacks."""
+        shutdown = GracefulShutdown()
+        callback = MagicMock()
+        shutdown.register_cleanup(callback)
+
+        async with shutdown:
+            pass
+
+        callback.assert_called_once()
+
+
+class TestRunWithGracefulShutdown:
+    """Tests for the run_with_graceful_shutdown helper."""
+
+    async def test_runs_coroutine_to_completion(self) -> None:
+        """Should run the coroutine to completion if no shutdown."""
+        result = []
+
+        async def my_coro() -> None:
+            result.append("done")
+
+        await run_with_graceful_shutdown(my_coro(), timeout=1.0)
+
+        assert result == ["done"]
+
+    async def test_stops_on_shutdown_signal(self) -> None:
+        """Should stop when shutdown is signaled."""
+        result = []
+
+        async def long_running() -> None:
+            try:
+                await asyncio.sleep(10.0)
+            except asyncio.CancelledError:
+                result.append("cancelled")
+                raise
+
+        # Create a wrapper that will trigger shutdown
+        async def run_with_interrupt() -> None:
+            async def trigger_shutdown() -> None:
+                await asyncio.sleep(0.1)
+                # We can't easily trigger a signal in tests, so we test the task
+                # completion path instead
+                pass
+
+            # Run both tasks
+            task = asyncio.create_task(long_running())
+            asyncio.create_task(trigger_shutdown())
+
+            await asyncio.sleep(0.05)
+            task.cancel()
+
+            with pytest.raises(asyncio.CancelledError):
+                await task
+
+            result.append("finished")
+
+        await run_with_interrupt()
+        assert "finished" in result
+
+
+class TestShutdownSignals:
+    """Tests for shutdown signal configuration."""
+
+    def test_shutdown_signals_includes_sigterm(self) -> None:
+        """SHUTDOWN_SIGNALS should include SIGTERM."""
+        assert signal.SIGTERM in SHUTDOWN_SIGNALS
+
+    def test_shutdown_signals_includes_sigint(self) -> None:
+        """SHUTDOWN_SIGNALS should include SIGINT."""
+        assert signal.SIGINT in SHUTDOWN_SIGNALS

uv.lock

@@ -126,6 +126,15 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/fb/76/641ae371508676492379f16e2fa48f4e2c11741bd63c48be4b12a6b09cba/aiosignal-1.4.0-py3-none-any.whl", hash = "sha256:053243f8b92b990551949e63930a839ff0cf0b0ebbe0597b0f3fb19e1a0fe82e", size = 7490, upload-time = "2025-07-03T22:54:42.156Z" },
 ]
 
+[[package]]
+name = "aiosqlite"
+version = "0.22.1"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/4e/8a/64761f4005f17809769d23e518d915db74e6310474e733e3593cfc854ef1/aiosqlite-0.22.1.tar.gz", hash = "sha256:043e0bd78d32888c0a9ca90fc788b38796843360c855a7262a532813133a0650", size = 14821, upload-time = "2025-12-23T19:25:43.997Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/00/b7/e3bf5133d697a08128598c8d0abc5e16377b51465a33756de24fa7dee953/aiosqlite-0.22.1-py3-none-any.whl", hash = "sha256:21c002eb13823fad740196c5a2e9d8e62f6243bd9e7e4a1f87fb5e44ecb4fceb", size = 17405, upload-time = "2025-12-23T19:25:42.139Z" },
+]
+
 [[package]]
 name = "alembic"
 version = "1.17.2"
@@ -1538,6 +1547,7 @@ dependencies = [
     { name = "prometheus-client" },
     { name = "py-clob-client" },
     { name = "pydantic" },
+    { name = "pydantic-settings" },
     { name = "python-dotenv" },
     { name = "redis" },
     { name = "scikit-learn" },
@@ -1548,6 +1558,7 @@ dependencies = [
 
 [package.optional-dependencies]
 dev = [
+    { name = "aiosqlite" },
     { name = "mypy" },
     { name = "pre-commit" },
     { name = "pytest" },
@@ -1559,6 +1570,7 @@ dev = [
 [package.metadata]
 requires-dist = [
     { name = "aiohttp", specifier = ">=3.9.0" },
+    { name = "aiosqlite", marker = "extra == 'dev'", specifier = ">=0.19.0" },
     { name = "alembic", specifier = ">=1.13.0" },
     { name = "httpx", specifier = ">=0.25.0" },
     { name = "mypy", marker = "extra == 'dev'", specifier = ">=1.7.0" },
@@ -1567,6 +1579,7 @@ requires-dist = [
     { name = "prometheus-client", specifier = ">=0.19.0" },
     { name = "py-clob-client", specifier = ">=0.1.0" },
     { name = "pydantic", specifier = ">=2.0.0" },
+    { name = "pydantic-settings", specifier = ">=2.0.0" },
     { name = "pytest", marker = "extra == 'dev'", specifier = ">=7.0.0" },
     { name = "pytest-asyncio", marker = "extra == 'dev'", specifier = ">=0.21.0" },
     { name = "pytest-cov", marker = "extra == 'dev'", specifier = ">=4.0.0" },
@@ -1892,6 +1905,20 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/36/c7/cfc8e811f061c841d7990b0201912c3556bfeb99cdcb7ed24adc8d6f8704/pydantic_core-2.41.5-pp311-pypy311_pp73-win_amd64.whl", hash = "sha256:56121965f7a4dc965bff783d70b907ddf3d57f6eba29b6d2e5dabfaf07799c51", size = 2145302, upload-time = "2025-11-04T13:43:46.64Z" },
 ]
 
+[[package]]
+name = "pydantic-settings"
+version = "2.12.0"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "pydantic" },
+    { name = "python-dotenv" },
+    { name = "typing-inspection" },
+]
+sdist = { url = "https://files.pythonhosted.org/packages/43/4b/ac7e0aae12027748076d72a8764ff1c9d82ca75a7a52622e67ed3f765c54/pydantic_settings-2.12.0.tar.gz", hash = "sha256:005538ef951e3c2a68e1c08b292b5f2e71490def8589d4221b95dab00dafcfd0", size = 194184, upload-time = "2025-11-10T14:25:47.013Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/c1/60/5d4751ba3f4a40a6891f24eec885f51afd78d208498268c734e256fb13c4/pydantic_settings-2.12.0-py3-none-any.whl", hash = "sha256:fddb9fd99a5b18da837b29710391e945b1e30c135477f484084ee513adb93809", size = 51880, upload-time = "2025-11-10T14:25:45.546Z" },
+]
+
 [[package]]
 name = "pygments"
 version = "2.19.2"