chore: promote UAT to production (CAR-630)

Promotes UAT to main including PR #209 (N+1 UPC query fix with SQL containment).

UAT regression: passed (Deal Dottie)
Security review: passed (Stockboy Steve)
CI required checks: all green

Co-Authored-By: Paperclip <noreply@paperclip.ing>

.github/workflows/ci.yml

@@ -13,6 +13,7 @@ concurrency:
 permissions:
   contents: write
   packages: write
+  security-events: write
 
 env:
   REGISTRY: ghcr.io
@@ -151,17 +152,44 @@ jobs:
             type=raw,value=${{ steps.calver.outputs.version }},enable=${{ github.ref == 'refs/heads/main' }}
             type=raw,value=latest,enable=${{ github.ref == 'refs/heads/main' }}
 
-      - name: Build and push Docker image
+      - name: Build Docker image
         uses: docker/build-push-action@v6
         with:
           context: .
-          push: ${{ github.event_name == 'push' }}
+          load: true
           tags: ${{ steps.meta.outputs.tags }}
           labels: ${{ steps.meta.outputs.labels }}
           target: prod
           cache-from: type=gha
           cache-to: type=gha,mode=max
 
+      - name: Scan frontend image for vulnerabilities
+        uses: anchore/scan-action@v5
+        id: scan
+        with:
+          image: "${{ env.REGISTRY }}/${{ env.IMAGE_NAME }}:sha-${{ github.sha }}"
+          fail-build: true
+          severity-cutoff: high
+          only-fixed: "true"
+          output-format: sarif
+
+      - name: Upload frontend scan results to GitHub Security
+        uses: github/codeql-action/upload-sarif@v3
+        if: always()
+        with:
+          sarif_file: ${{ steps.scan.outputs.sarif }}
+
+      - name: Push Docker image
+        if: github.event_name == 'push'
+        uses: docker/build-push-action@v6
+        with:
+          context: .
+          push: true
+          tags: ${{ steps.meta.outputs.tags }}
+          labels: ${{ steps.meta.outputs.labels }}
+          target: prod
+          cache-from: type=gha
+
       - name: Create git tag
         if: github.event_name == 'push' && github.ref == 'refs/heads/main'
         run: |
@@ -221,14 +249,43 @@ jobs:
             type=raw,value=${{ steps.calver.outputs.version }},enable=${{ github.ref == 'refs/heads/main' }}
             type=raw,value=latest,enable=${{ github.ref == 'refs/heads/main' }}
 
-      - name: Build and push auth Docker image
+      - name: Build Docker image
         uses: docker/build-push-action@v6
         with:
           context: ./auth
           file: ./auth/Dockerfile
-          push: ${{ github.event_name == 'push' }}
+          load: true
           tags: ${{ steps.meta.outputs.tags }}
           labels: ${{ steps.meta.outputs.labels }}
+          cache-from: type=gha
+          cache-to: type=gha,mode=max
+
+      - name: Scan auth image for vulnerabilities
+        uses: anchore/scan-action@v5
+        id: scan
+        with:
+          image: "${{ env.REGISTRY }}/${{ env.AUTH_IMAGE_NAME }}:sha-${{ github.sha }}"
+          fail-build: true
+          severity-cutoff: high
+          only-fixed: "true"
+          output-format: sarif
+
+      - name: Upload auth scan results to GitHub Security
+        uses: github/codeql-action/upload-sarif@v3
+        if: always()
+        with:
+          sarif_file: ${{ steps.scan.outputs.sarif }}
+
+      - name: Push Docker image
+        if: github.event_name == 'push'
+        uses: docker/build-push-action@v6
+        with:
+          context: ./auth
+          file: ./auth/Dockerfile
+          push: true
+          tags: ${{ steps.meta.outputs.tags }}
+          labels: ${{ steps.meta.outputs.labels }}
+          cache-from: type=gha
 
   build-and-push-receiptwitness:
     runs-on: runners-cartsnitch
@@ -278,14 +335,43 @@ jobs:
             type=raw,value=${{ steps.calver.outputs.version }},enable=${{ github.ref == 'refs/heads/main' }}
             type=raw,value=latest,enable=${{ github.ref == 'refs/heads/main' }}
 
-      - name: Build and push receiptwitness image
+      - name: Build Docker image
         uses: docker/build-push-action@v6
         with:
           context: .
           file: ./receiptwitness/Dockerfile
-          push: ${{ github.event_name == 'push' }}
+          load: true
           tags: ${{ steps.meta.outputs.tags }}
           labels: ${{ steps.meta.outputs.labels }}
+          cache-from: type=gha
+          cache-to: type=gha,mode=max
+
+      - name: Scan receiptwitness image for vulnerabilities
+        uses: anchore/scan-action@v5
+        id: scan
+        with:
+          image: "${{ env.REGISTRY }}/${{ env.RECEIPTWITNESS_IMAGE_NAME }}:sha-${{ github.sha }}"
+          fail-build: true
+          severity-cutoff: high
+          only-fixed: "true"
+          output-format: sarif
+
+      - name: Upload receiptwitness scan results to GitHub Security
+        uses: github/codeql-action/upload-sarif@v3
+        if: always()
+        with:
+          sarif_file: ${{ steps.scan.outputs.sarif }}
+
+      - name: Push Docker image
+        if: github.event_name == 'push'
+        uses: docker/build-push-action@v6
+        with:
+          context: .
+          file: ./receiptwitness/Dockerfile
+          push: true
+          tags: ${{ steps.meta.outputs.tags }}
+          labels: ${{ steps.meta.outputs.labels }}
+          cache-from: type=gha
 
   build-and-push-api:
     runs-on: runners-cartsnitch
@@ -335,14 +421,43 @@ jobs:
             type=raw,value=${{ steps.calver.outputs.version }},enable=${{ github.ref == 'refs/heads/main' }}
             type=raw,value=latest,enable=${{ github.ref == 'refs/heads/main' }}
 
-      - name: Build and push API Docker image
+      - name: Build Docker image
         uses: docker/build-push-action@v6
         with:
           context: ./api
           file: ./api/Dockerfile
-          push: ${{ github.event_name == 'push' }}
+          load: true
           tags: ${{ steps.meta.outputs.tags }}
           labels: ${{ steps.meta.outputs.labels }}
+          cache-from: type=gha
+          cache-to: type=gha,mode=max
+
+      - name: Scan api image for vulnerabilities
+        uses: anchore/scan-action@v5
+        id: scan
+        with:
+          image: "${{ env.REGISTRY }}/${{ env.API_IMAGE_NAME }}:sha-${{ github.sha }}"
+          fail-build: true
+          severity-cutoff: high
+          only-fixed: "true"
+          output-format: sarif
+
+      - name: Upload api scan results to GitHub Security
+        uses: github/codeql-action/upload-sarif@v3
+        if: always()
+        with:
+          sarif_file: ${{ steps.scan.outputs.sarif }}
+
+      - name: Push Docker image
+        if: github.event_name == 'push'
+        uses: docker/build-push-action@v6
+        with:
+          context: ./api
+          file: ./api/Dockerfile
+          push: true
+          tags: ${{ steps.meta.outputs.tags }}
+          labels: ${{ steps.meta.outputs.labels }}
+          cache-from: type=gha
 
   deploy-dev:
     runs-on: runners-cartsnitch

Dockerfile

@@ -1,6 +1,6 @@
 # Stage 1: Build
 FROM node:20-alpine AS build
-
+RUN apk update && apk upgrade --no-cache
 WORKDIR /app
 
 COPY package.json package-lock.json ./
@@ -11,6 +11,9 @@ RUN npm run build
 
 # Stage 2: Production — uses nginxinc/nginx-unprivileged which runs as non-root (UID 101)
 FROM nginxinc/nginx-unprivileged:stable-alpine AS prod
+USER root
+RUN apk update && apk upgrade --no-cache
+USER 101
 
 COPY --from=build /app/dist /usr/share/nginx/html
 COPY nginx.conf /etc/nginx/conf.d/default.conf

api/Dockerfile

@@ -1,6 +1,6 @@
 FROM python:3.12-slim AS build
 
-RUN apt-get update && apt-get install -y --no-install-recommends \
+RUN apt-get update && apt-get upgrade -y && apt-get install -y --no-install-recommends \
     libpq-dev \
     build-essential \
     && rm -rf /var/lib/apt/lists/*
@@ -12,7 +12,7 @@ RUN pip install --no-cache-dir --prefix=/install .
 
 FROM python:3.12-slim AS prod
 
-RUN apt-get update && apt-get install -y --no-install-recommends libpq5 && rm -rf /var/lib/apt/lists/*
+RUN apt-get update && apt-get upgrade -y && apt-get install -y --no-install-recommends libpq5 && rm -rf /var/lib/apt/lists/*
 
 WORKDIR /app
 RUN adduser --system --group --uid 1000 app

api/alembic/versions/009_add_gin_index_upc_variants.py

@@ -0,0 +1,38 @@
+"""Add GIN index on upc_variants and alter column to JSONB.
+
+Revision ID: 009_add_gin_index_upc_variants
+Revises: 008_create_domain_tables
+Create Date: 2026-04-14
+"""
+
+import sqlalchemy as sa
+from alembic import op
+
+revision = "009_add_gin_index_upc_variants"
+down_revision = "008_create_domain_tables"
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    op.alter_column(
+        "normalized_products",
+        "upc_variants",
+        type_=sa.dialects.postgresql.JSONB(),
+        postgresql_using="upc_variants::jsonb",
+    )
+    op.create_index(
+        "ix_normalized_products_upc_variants_gin",
+        "normalized_products",
+        ["upc_variants"],
+        postgresql_using="gin",
+    )
+
+
+def downgrade() -> None:
+    op.drop_index("ix_normalized_products_upc_variants_gin", table_name="normalized_products")
+    op.alter_column(
+        "normalized_products",
+        "upc_variants",
+        type_=sa.JSON(),
+    )

api/src/cartsnitch_api/cache.py

@@ -1,26 +1,51 @@
 """Redis/DragonflyDB caching helpers."""
 
+import redis.asyncio as redis
+
 from cartsnitch_api.config import settings
 
 
 class CacheClient:
-    """Stub for Redis/DragonflyDB caching.
+    """Redis/DragonflyDB caching with connection pooling.
 
     Will be used for expensive queries: price trends, product comparisons.
     Cache invalidation via Redis pub/sub events from other services.
     """
 
     def __init__(self) -> None:
-        self.url = settings.redis_url
+        self._pool: redis.ConnectionPool | None = None
+        self._client: redis.Redis | None = None
+
+    async def initialize(self) -> None:
+        """Initialize the Redis connection pool."""
+        self._pool = redis.ConnectionPool.from_url(
+            settings.redis_url,
+            max_connections=20,
+            decode_responses=True,
+        )
+        self._client = redis.Redis(connection_pool=self._pool)
+
+    async def close(self) -> None:
+        """Close the Redis connection pool."""
+        if self._client:
+            await self._client.aclose()
+        if self._pool:
+            await self._pool.aclose()
 
     async def get(self, key: str) -> str | None:
-        # TODO: implement with redis-py async
-        return None
+        if not self._client:
+            return None
+        return await self._client.get(key)
 
     async def set(self, key: str, value: str, ttl_seconds: int = 300) -> None:
-        # TODO: implement with redis-py async
-        pass
+        if not self._client:
+            return
+        await self._client.set(key, value, ex=ttl_seconds)
 
     async def delete(self, key: str) -> None:
-        # TODO: implement with redis-py async
-        pass
+        if not self._client:
+            return
+        await self._client.delete(key)
+
+
+cache_client = CacheClient()

api/src/cartsnitch_api/database.py

@@ -6,7 +6,14 @@ from sqlalchemy.ext.asyncio import AsyncSession, async_sessionmaker, create_asyn
 
 from cartsnitch_api.config import settings
 
-engine = create_async_engine(settings.database_url, echo=False)
+engine = create_async_engine(
+    settings.database_url,
+    echo=False,
+    pool_size=10,
+    max_overflow=20,
+    pool_pre_ping=True,
+    pool_recycle=3600,
+)
 async_session_factory = async_sessionmaker(engine, class_=AsyncSession, expire_on_commit=False)
 
 
@@ -14,3 +21,8 @@ async def get_db() -> AsyncGenerator[AsyncSession, None]:
     """FastAPI dependency that yields an async DB session."""
     async with async_session_factory() as session:
         yield session
+
+
+async def dispose_engine() -> None:
+    """Dispose the database engine, closing all pooled connections."""
+    await engine.dispose()

api/src/cartsnitch_api/main.py

@@ -5,6 +5,8 @@ from contextlib import asynccontextmanager
 from fastapi import APIRouter, FastAPI
 
 from cartsnitch_api.auth.routes import router as auth_router
+from cartsnitch_api.cache import cache_client
+from cartsnitch_api.database import dispose_engine
 from cartsnitch_api.middleware.cors import add_cors_middleware
 from cartsnitch_api.middleware.error_handler import add_error_handlers, add_error_monitor_middleware
 from cartsnitch_api.middleware.rate_limit import add_rate_limit_middleware
@@ -23,9 +25,10 @@ from cartsnitch_api.routes.user import router as user_router
 
 @asynccontextmanager
 async def lifespan(app: FastAPI):
-    # TODO: initialize DB session pool, Redis connection, service clients
+    await cache_client.initialize()
     yield
-    # TODO: cleanup connections
+    await cache_client.close()
+    await dispose_engine()
 
 
 def create_app() -> FastAPI:

api/src/cartsnitch_api/middleware/cors.py

@@ -11,6 +11,6 @@ def add_cors_middleware(app: FastAPI) -> None:
         CORSMiddleware,
         allow_origins=settings.cors_origins,
         allow_credentials=True,
-        allow_methods=["*"],
-        allow_headers=["*"],
+        allow_methods=["GET", "POST", "PUT", "DELETE", "PATCH", "OPTIONS"],
+        allow_headers=["Content-Type", "Authorization", "Accept", "Origin", "X-Requested-With"],
     )

api/src/cartsnitch_api/middleware/rate_limit.py

@@ -4,6 +4,7 @@ Uses in-memory sliding window as fallback, Redis/DragonflyDB when available.
 Per-IP limiting on public endpoints, per-token limiting on authenticated endpoints.
 """
 
+import hashlib
 import time
 from collections import defaultdict
 from threading import Lock
@@ -71,8 +72,8 @@ def _get_rate_limit_key(request: Request) -> tuple[str, _SlidingWindowCounter]:
     auth_header = request.headers.get("authorization", "")
     if auth_header.startswith("Bearer "):
         token = auth_header[7:]
-        # Use last 16 chars of token as key to avoid storing full tokens
-        return f"token:{token[-16:]}", _auth_limiter
+        token_hash = hashlib.sha256(token.encode()).hexdigest()
+        return f"token:{token_hash}", _auth_limiter
 
     # Fallback to IP for unauthenticated non-public endpoints
     return f"ip:{_get_client_ip(request)}", _public_limiter

api/tests/test_middleware/test_rate_limit.py

@@ -1,8 +1,10 @@
 """Tests for rate limiting middleware."""
 
+from unittest.mock import MagicMock
+
 import pytest
 
-from cartsnitch_api.middleware.rate_limit import _SlidingWindowCounter
+from cartsnitch_api.middleware.rate_limit import _SlidingWindowCounter, _get_rate_limit_key
 
 
 class TestSlidingWindowCounter:
@@ -53,3 +55,32 @@ async def test_health_skips_rate_limit(client):
     resp = await client.get("/health")
     assert resp.status_code == 200
     assert "x-ratelimit-limit" not in resp.headers
+
+
+class TestGetRateLimitKey:
+    def _make_request(self, auth_header: str = "") -> MagicMock:
+        req = MagicMock()
+        req.url.path = "/purchases"
+        req.headers = {"authorization": auth_header} if auth_header else {}
+        return req
+
+    def test_distinct_tokens_produce_distinct_keys(self):
+        req1 = self._make_request("Bearer token_alpha_12345")
+        req2 = self._make_request("Bearer token_beta_67890")
+        key1, _ = _get_rate_limit_key(req1)
+        key2, _ = _get_rate_limit_key(req2)
+        assert key1 != key2
+
+    def test_same_token_produces_same_key(self):
+        req1 = self._make_request("Bearer same_token_value_abc")
+        req2 = self._make_request("Bearer same_token_value_abc")
+        key1, _ = _get_rate_limit_key(req1)
+        key2, _ = _get_rate_limit_key(req2)
+        assert key1 == key2
+
+    def test_key_does_not_contain_raw_token_suffix(self):
+        raw_token = "my_secret_jwt_token_xyz"
+        req = self._make_request(f"Bearer {raw_token}")
+        key, _ = _get_rate_limit_key(req)
+        assert raw_token[-16:] not in key
+        assert raw_token not in key

auth/Dockerfile

@@ -1,4 +1,5 @@
 FROM node:22-alpine AS builder
+RUN apk update && apk upgrade --no-cache
 WORKDIR /app
 COPY package.json package-lock.json* ./
 RUN npm ci
@@ -7,6 +8,7 @@ COPY src/ src/
 RUN npm run build
 
 FROM node:22-alpine
+RUN apk update && apk upgrade --no-cache
 WORKDIR /app
 ENV NODE_ENV=production
 COPY package.json package-lock.json* ./

auth/package-lock.json

@@ -941,9 +941,9 @@
       }
     },
     "node_modules/defu": {
-      "version": "6.1.4",
-      "resolved": "https://registry.npmjs.org/defu/-/defu-6.1.4.tgz",
-      "integrity": "sha512-mEQCMmwJu317oSz8CwdIOdwf3xMif1ttiM8LTufzc3g6kR+9Pe236twL8j3IYT1F7GfRgGcW6MWxzZjLIkuHIg==",
+      "version": "6.1.7",
+      "resolved": "https://registry.npmjs.org/defu/-/defu-6.1.7.tgz",
+      "integrity": "sha512-7z22QmUWiQ/2d0KkdYmANbRUVABpZ9SNYyH5vx6PZ+nE5bcC0l7uFvEfHlyld/HcGBFTL536ClDt3DEcSlEJAQ==",
       "license": "MIT"
     },
     "node_modules/delegates": {

auth/src/auth.ts

@@ -4,17 +4,23 @@ import pg from "pg";
 
 const { Pool } = pg;
 
-const pool = new Pool({
-  connectionString:
-    process.env.DATABASE_URL ??
-    "postgresql://cartsnitch:cartsnitch@localhost:5432/cartsnitch",
-});
-
 const secret = process.env.BETTER_AUTH_SECRET;
 if (!secret) {
   throw new Error("BETTER_AUTH_SECRET environment variable is required");
 }
 
+const databaseUrl = process.env.DATABASE_URL;
+if (!databaseUrl) {
+  console.warn(
+    "WARNING: DATABASE_URL is not set — using default localhost connection. " +
+    "Set DATABASE_URL for production deployments."
+  );
+}
+
+export const pool = new Pool({
+  connectionString: databaseUrl ?? "postgresql://cartsnitch:cartsnitch@localhost:5432/cartsnitch",
+});
+
 export const auth = betterAuth({
   database: pool,
   basePath: "/auth",

auth/src/index.ts

@@ -1,6 +1,6 @@
 import { createServer } from "node:http";
 import { toNodeHandler } from "better-auth/node";
-import { auth } from "./auth.js";
+import { auth, pool } from "./auth.js";
 
 const port = parseInt(process.env.PORT ?? "3001", 10);
 
@@ -9,8 +9,22 @@ const handler = toNodeHandler(auth);
 const server = createServer(async (req, res) => {
   // Health check
   if (req.url === "/health" && req.method === "GET") {
-    res.writeHead(200, { "Content-Type": "application/json" });
-    res.end(JSON.stringify({ status: "ok" }));
+    try {
+      const client = await pool.connect();
+      try {
+        await Promise.race([
+          client.query("SELECT 1"),
+          new Promise((_, reject) => setTimeout(() => reject(new Error("DB timeout")), 2000)),
+        ]);
+      } finally {
+        client.release();
+      }
+      res.writeHead(200, { "Content-Type": "application/json" });
+      res.end(JSON.stringify({ status: "ok", db: "connected" }));
+    } catch {
+      res.writeHead(503, { "Content-Type": "application/json" });
+      res.end(JSON.stringify({ status: "error", db: "unreachable" }));
+    }
     return;
   }
 

common/src/cartsnitch_common/models/product.py

@@ -3,6 +3,7 @@
 from typing import TYPE_CHECKING
 
 from sqlalchemy import JSON, String
+from sqlalchemy.dialects.postgresql import JSONB
 from sqlalchemy.orm import Mapped, mapped_column, relationship
 
 from cartsnitch_common.constants import ProductCategory, SizeUnit
@@ -26,7 +27,9 @@ class NormalizedProduct(UUIDPrimaryKeyMixin, TimestampMixin, Base):
     brand: Mapped[str | None] = mapped_column(String(200))
     size: Mapped[str | None] = mapped_column(String(50))
     size_unit: Mapped[SizeUnit | None] = mapped_column(String(10))
-    upc_variants: Mapped[list[str] | None] = mapped_column(JSON, default=list)
+    upc_variants: Mapped[list[str] | None] = mapped_column(
+        JSON().with_variant(JSONB(), "postgresql"), default=list
+    )
 
     # Relationships
     purchase_items: Mapped[list["PurchaseItem"]] = relationship(back_populates="normalized_product")

nginx.conf

@@ -9,6 +9,12 @@ server {
     gzip_types text/plain text/css application/json application/javascript text/xml application/xml application/xml+rss text/javascript image/svg+xml;
     gzip_min_length 256;
 
+    # Security headers
+    add_header X-Frame-Options "SAMEORIGIN" always;
+    add_header X-Content-Type-Options "nosniff" always;
+    add_header Referrer-Policy "strict-origin-when-cross-origin" always;
+    add_header Content-Security-Policy "default-src 'self'; script-src 'self'; style-src 'self' 'unsafe-inline'; img-src 'self' data: https:; font-src 'self'; connect-src 'self' https://*.cartsnitch.com https://*.farh.net; frame-ancestors 'self'" always;
+
     # Health endpoint for K8s probes
     location /health {
         access_log off;

package-lock.json

@@ -9805,9 +9805,9 @@
       }
     },
     "node_modules/vite": {
-      "version": "6.4.1",
-      "resolved": "https://registry.npmjs.org/vite/-/vite-6.4.1.tgz",
-      "integrity": "sha512-+Oxm7q9hDoLMyJOYfUYBuHQo+dkAloi33apOPP56pzj+vsdJDzr+j1NISE5pyaAuKL4A3UD34qd0lx5+kfKp2g==",
+      "version": "6.4.2",
+      "resolved": "https://registry.npmjs.org/vite/-/vite-6.4.2.tgz",
+      "integrity": "sha512-2N/55r4JDJ4gdrCvGgINMy+HH3iRpNIz8K6SFwVsA+JbQScLiC+clmAxBgwiSPgcG9U15QmvqCGWzMbqda5zGQ==",
       "devOptional": true,
       "license": "MIT",
       "dependencies": {

receiptwitness/Dockerfile

@@ -5,7 +5,7 @@ WORKDIR /app
 
 # build-essential and libpq-dev are needed to compile any C-extension wheels
 # (e.g. psycopg2 fallback).  No git needed — common/ is copied from the repo root.
-RUN apt-get update && apt-get install -y --no-install-recommends \
+RUN apt-get update && apt-get upgrade -y && apt-get install -y --no-install-recommends \
     libpq-dev \
     build-essential \
     && rm -rf /var/lib/apt/lists/*
@@ -25,7 +25,7 @@ FROM python:3.12-slim AS prod
 WORKDIR /app
 
 # Install Playwright system dependencies for Chromium
-RUN apt-get update && apt-get install -y --no-install-recommends \
+RUN apt-get update && apt-get upgrade -y && apt-get install -y --no-install-recommends \
     libnss3 \
     libatk1.0-0 \
     libatk-bridge2.0-0 \

receiptwitness/src/receiptwitness/config.py

@@ -1,8 +1,12 @@
 """Service-specific configuration for ReceiptWitness."""
 
+from pydantic import model_validator
 from pydantic_settings import BaseSettings
 
 
+_PLACEHOLDER_VALUES = {"change-me-in-production"}
+
+
 class ReceiptWitnessSettings(BaseSettings):
     model_config = {"env_prefix": "RW_"}
 
@@ -30,5 +34,34 @@ class ReceiptWitnessSettings(BaseSettings):
     # Mailgun inbound email webhook
     mailgun_webhook_signing_key: str = ""
 
+    @model_validator(mode="after")
+    def validate_required_vars(self):
+        errors = []
+        if not self.session_encryption_key or self.session_encryption_key in _PLACEHOLDER_VALUES:
+            errors.append(
+                "RW_SESSION_ENCRYPTION_KEY must be set to a secure value. "
+                'Generate one with: python -c "from cryptography.fernet import Fernet; print(Fernet.generate_key().decode())"'
+            )
+        if self.notifications_enabled and not self.resend_api_key:
+            errors.append(
+                "RW_RESEND_API_KEY must be set when RW_NOTIFICATIONS_ENABLED=true. "
+                "Get an API key from https://resend.com/api-keys"
+            )
+        if errors:
+            raise ValueError(
+                "ReceiptWitness startup failed — missing required config:\n"
+                + "\n".join(f"  - {e}" for e in errors)
+            )
+        return self
 
-settings = ReceiptWitnessSettings()
+
+class _LazySettings:
+    _instance: ReceiptWitnessSettings | None = None
+
+    def __getattr__(self, name: str):
+        if _LazySettings._instance is None:
+            _LazySettings._instance = ReceiptWitnessSettings()
+        return getattr(_LazySettings._instance, name)
+
+
+settings = _LazySettings()

receiptwitness/src/receiptwitness/pipeline/normalization.py

@@ -5,12 +5,14 @@ Matches products across retailers by:
 2. Fuzzy name matching via token-based Jaccard similarity (lower confidence)
 """
 
+import json
 import re
 from dataclasses import dataclass
 from enum import StrEnum
 
 from cartsnitch_common.models.product import NormalizedProduct
-from sqlalchemy import select
+from sqlalchemy import cast, func, select, String
+from sqlalchemy.dialects.postgresql import JSONB
 from sqlalchemy.orm import Session
 
 
@@ -96,17 +98,24 @@ def jaccard_similarity(a: str, b: str) -> float:
 def match_by_upc(session: Session, upc: str) -> MatchResult | None:
     """Find a normalized product by exact UPC match.
 
-    Loads products with upc_variants and checks membership in Python
-    for cross-database compatibility (works on both PostgreSQL and SQLite).
+    Uses PostgreSQL JSONB containment (@>) for production efficiency.
+    Falls back to LIKE on SQLite for test compatibility.
     """
-    # TODO: Use PostgreSQL JSON containment query (@>) for production.
-    # Current approach loads all products into memory — acceptable for tests
-    # and small datasets, but will not scale.
-    stmt = select(NormalizedProduct).where(NormalizedProduct.upc_variants.is_not(None))
-    products = session.execute(stmt).scalars().all()
-    for product in products:
-        if product.upc_variants and upc in product.upc_variants:
-            return MatchResult(product=product, confidence=1.0, method=MatchMethod.UPC)
+    dialect_name = session.bind.dialect.name if session.bind else "default"
+    if dialect_name == "postgresql":
+        stmt = select(NormalizedProduct).where(
+            cast(NormalizedProduct.upc_variants, JSONB).op("@>")(
+                func.cast(json.dumps([upc]), JSONB)
+            )
+        )
+    else:
+        stmt = select(NormalizedProduct).where(
+            NormalizedProduct.upc_variants.is_not(None),
+            cast(NormalizedProduct.upc_variants, String).contains(upc),
+        )
+    product = session.execute(stmt).scalars().first()
+    if product:
+        return MatchResult(product=product, confidence=1.0, method=MatchMethod.UPC)
     return None
 
 

receiptwitness/tests/conftest.py

@@ -1,12 +1,16 @@
 """Shared test fixtures."""
 
 import json
+import os
 from pathlib import Path
 
 import pytest
 
 FIXTURES_DIR = Path(__file__).parent / "fixtures"
 
+os.environ.setdefault("RW_SESSION_ENCRYPTION_KEY", "test-secret-key-for-unit-tests-only-32bytes!")
+os.environ.setdefault("RW_MAILGUN_WEBHOOK_SIGNING_KEY", "test-mailgun-signing-key")
+
 
 @pytest.fixture
 def meijer_receipt_data() -> dict:

receiptwitness/tests/test_config.py

@@ -0,0 +1,46 @@
+import pytest
+from receiptwitness.config import ReceiptWitnessSettings
+
+
+def test_valid_config():
+    s = ReceiptWitnessSettings(
+        session_encryption_key="7reF42nmTwbdN21PBoubGp7h_FU8qSimstmlaMLoRK8="
+    )
+    assert s.session_encryption_key
+
+
+def test_missing_session_encryption_key_raises():
+    with pytest.raises(ValueError, match="RW_SESSION_ENCRYPTION_KEY"):
+        ReceiptWitnessSettings(session_encryption_key="")
+
+
+def test_placeholder_session_encryption_key_raises():
+    with pytest.raises(ValueError, match="RW_SESSION_ENCRYPTION_KEY"):
+        ReceiptWitnessSettings(session_encryption_key="change-me-in-production")
+
+
+def test_notifications_enabled_without_resend_key_raises():
+    with pytest.raises(ValueError, match="RW_RESEND_API_KEY"):
+        ReceiptWitnessSettings(
+            session_encryption_key="7reF42nmTwbdN21PBoubGp7h_FU8qSimstmlaMLoRK8=",
+            notifications_enabled=True,
+            resend_api_key="",
+        )
+
+
+def test_notifications_disabled_without_resend_key_ok():
+    s = ReceiptWitnessSettings(
+        session_encryption_key="7reF42nmTwbdN21PBoubGp7h_FU8qSimstmlaMLoRK8=",
+        notifications_enabled=False,
+        resend_api_key="",
+    )
+    assert s.notifications_enabled is False
+
+
+def test_notifications_enabled_with_resend_key_ok():
+    s = ReceiptWitnessSettings(
+        session_encryption_key="7reF42nmTwbdN21PBoubGp7h_FU8qSimstmlaMLoRK8=",
+        notifications_enabled=True,
+        resend_api_key="re_test_1234567890",
+    )
+    assert s.resend_api_key == "re_test_1234567890"