fix: add startup validation to ReceiptWitness config

Add Pydantic model_validator to ReceiptWitnessSettings that fails fast
if session_encryption_key is missing or a placeholder value. Conditional
validation for resend_api_key when notifications_enabled=true.

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

api/alembic/versions/009_add_gin_index_upc_variants.py

@@ -1,38 +0,0 @@
-"""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/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
+        token_hash = hashlib.sha256(token.encode()).hexdigest()
-        return f"token:{token[-16:]}", _auth_limiter
+        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

common/src/cartsnitch_common/models/product.py

@@ -3,7 +3,6 @@
 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
@@ -27,9 +26,7 @@ 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(
+    upc_variants: Mapped[list[str] | None] = mapped_column(JSON, default=list)
-        JSON().with_variant(JSONB(), "postgresql"), default=list
-    )
 
     # Relationships
     purchase_items: Mapped[list["PurchaseItem"]] = relationship(back_populates="normalized_product")

package-lock.json

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

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

@@ -5,14 +5,12 @@ 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 cast, func, select, String
+from sqlalchemy import select
-from sqlalchemy.dialects.postgresql import JSONB
 from sqlalchemy.orm import Session
 
 
@@ -98,24 +96,17 @@ 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.
 
-    Uses PostgreSQL JSONB containment (@>) for production efficiency.
+    Loads products with upc_variants and checks membership in Python
-    Falls back to LIKE on SQLite for test compatibility.
+    for cross-database compatibility (works on both PostgreSQL and SQLite).
     """
-    dialect_name = session.bind.dialect.name if session.bind else "default"
+    # TODO: Use PostgreSQL JSON containment query (@>) for production.
-    if dialect_name == "postgresql":
+    # Current approach loads all products into memory — acceptable for tests
-        stmt = select(NormalizedProduct).where(
+    # and small datasets, but will not scale.
-            cast(NormalizedProduct.upc_variants, JSONB).op("@>")(
+    stmt = select(NormalizedProduct).where(NormalizedProduct.upc_variants.is_not(None))
-                func.cast(json.dumps([upc]), JSONB)
+    products = session.execute(stmt).scalars().all()
-            )
+    for product in products:
-        )
+        if product.upc_variants and upc in product.upc_variants:
-    else:
+            return MatchResult(product=product, confidence=1.0, method=MatchMethod.UPC)
-        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"