security: rotate bootstrap and clean workspace

backend/src/scripts/init_auth_db.py

@@ -8,8 +8,10 @@
 # @INVARIANT: Safe to run multiple times (idempotent).
 
 # [SECTION: IMPORTS]
+import os
 import sys
 from pathlib import Path
+from cryptography.fernet import Fernet
 
 # Add src to path
 sys.path.append(str(Path(__file__).parent.parent.parent))
@@ -19,6 +21,41 @@ from src.core.logger import logger, belief_scope
 from src.scripts.seed_permissions import seed_permissions
 # [/SECTION]
 
+ENV_FILE_PATH = Path(__file__).resolve().parents[2] / ".env"
+
+
+# [DEF:ensure_encryption_key:Function]
+# @PURPOSE: Ensure backend runtime has a persistent Fernet encryption key during first-time installation.
+# @PRE: Backend root is writable or ENCRYPTION_KEY is already provided via environment.
+# @POST: ENCRYPTION_KEY exists in process environment or backend/.env.
+def ensure_encryption_key(env_file_path: Path = ENV_FILE_PATH) -> str:
+    existing_key = os.getenv("ENCRYPTION_KEY", "").strip()
+    if existing_key:
+        Fernet(existing_key.encode())
+        logger.info("ENCRYPTION_KEY already provided via environment; skipping generation.")
+        return existing_key
+
+    if env_file_path.exists():
+        for raw_line in env_file_path.read_text(encoding="utf-8").splitlines():
+            if raw_line.startswith("ENCRYPTION_KEY="):
+                persisted_key = raw_line.partition("=")[2].strip()
+                if persisted_key:
+                    Fernet(persisted_key.encode())
+                    os.environ["ENCRYPTION_KEY"] = persisted_key
+                    logger.info(f"Loaded existing ENCRYPTION_KEY from {env_file_path}.")
+                    return persisted_key
+
+    generated_key = Fernet.generate_key().decode()
+    with env_file_path.open("a", encoding="utf-8") as env_file:
+        if env_file.tell() > 0:
+            env_file.write("\n")
+        env_file.write(f"ENCRYPTION_KEY={generated_key}\n")
+
+    os.environ["ENCRYPTION_KEY"] = generated_key
+    logger.info(f"Generated ENCRYPTION_KEY and persisted it to {env_file_path}.")
+    return generated_key
+# [/DEF:ensure_encryption_key:Function]
+
 # [DEF:run_init:Function]
 # @PURPOSE: Main entry point for the initialization script.
 # @POST:    auth.db is initialized with the correct schema and seeded permissions.
@@ -26,6 +63,7 @@ def run_init():
     with belief_scope("init_auth_db"):
         logger.info("Initializing authentication database...")
         try:
+            ensure_encryption_key()
             init_db()
             logger.info("Authentication database initialized successfully.")
             
@@ -40,4 +78,4 @@ def run_init():
 if __name__ == "__main__":
     run_init()
 
-# [/DEF:backend.src.scripts.init_auth_db:Module]
+# [/DEF:backend.src.scripts.init_auth_db:Module]

backend/src/services/__tests__/test_encryption_manager.py

@@ -26,8 +26,7 @@ class TestEncryptionManager:
         """Construct EncryptionManager directly using Fernet (avoids relative import chain)."""
         # Re-implement the same logic as EncryptionManager to avoid import issues
         # with the llm_provider module's relative imports
-        import os
-        key = os.getenv("ENCRYPTION_KEY", "REMOVED_HISTORICAL_SECRET_DO_NOT_USE").encode()
+        key = Fernet.generate_key()
         fernet = Fernet(key)
 
         class EncryptionManager:
@@ -99,6 +98,18 @@ class TestEncryptionManager:
         assert decrypted == ""
     # [/DEF:test_encrypt_empty_string:Function]
 
+    # [DEF:test_missing_key_fails_fast:Function]
+    # @PURPOSE: Missing ENCRYPTION_KEY must abort initialization instead of using a fallback secret.
+    # @PRE: ENCRYPTION_KEY is unset.
+    # @POST: RuntimeError raised during EncryptionManager construction.
+    def test_missing_key_fails_fast(self):
+        from src.services.llm_provider import EncryptionManager
+
+        with patch.dict("os.environ", {}, clear=True):
+            with pytest.raises(RuntimeError, match="ENCRYPTION_KEY must be set"):
+                EncryptionManager()
+    # [/DEF:test_missing_key_fails_fast:Function]
+
     # [DEF:test_custom_key_roundtrip:Function]
     # @PURPOSE: Custom Fernet key produces valid roundtrip.
     # @PRE: Generated Fernet key.

backend/src/services/llm_provider.py

@@ -6,18 +6,35 @@
 # @RELATION: DEPENDS_ON -> backend.src.core.database
 # @RELATION: DEPENDS_ON -> backend.src.models.llm
 
-from typing import List, Optional
+from typing import List, Optional, TYPE_CHECKING
 from sqlalchemy.orm import Session
 from ..models.llm import LLMProvider
-from ..plugins.llm_analysis.models import LLMProviderConfig
 from ..core.logger import belief_scope, logger
 from cryptography.fernet import Fernet
 import os
 
+if TYPE_CHECKING:
+    from ..plugins.llm_analysis.models import LLMProviderConfig
+
+# [DEF:_require_fernet_key:Function]
+# @TIER: CRITICAL
+# @PURPOSE: Load and validate the Fernet key used for secret encryption.
+# @PRE: ENCRYPTION_KEY environment variable must be set to a valid Fernet key.
+# @POST: Returns validated key bytes ready for Fernet initialization.
+def _require_fernet_key() -> bytes:
+    raw_key = os.getenv("ENCRYPTION_KEY", "").strip()
+    if not raw_key:
+        raise RuntimeError("ENCRYPTION_KEY must be set to a valid Fernet key")
+
+    key = raw_key.encode()
+    Fernet(key)
+    return key
+# [/DEF:_require_fernet_key:Function]
+
 # [DEF:EncryptionManager:Class]
 # @TIER: CRITICAL
 # @PURPOSE: Handles encryption and decryption of sensitive data like API keys.
-# @INVARIANT: Uses a secret key from environment or a default one (fallback only for dev).
+# @INVARIANT: Uses only a validated secret key from environment.
 #
 # @TEST_CONTRACT: EncryptionManagerModel ->
 # {
@@ -33,10 +50,10 @@ import os
 class EncryptionManager:
     # [DEF:EncryptionManager.__init__:Function]
     # @PURPOSE: Initialize the encryption manager with a Fernet key.
-    # @PRE: ENCRYPTION_KEY env var must be set or use default dev key.
+    # @PRE: ENCRYPTION_KEY env var must be set to a valid Fernet key.
     # @POST: Fernet instance ready for encryption/decryption.
     def __init__(self):
-        self.key = os.getenv("ENCRYPTION_KEY", "REMOVED_HISTORICAL_SECRET_DO_NOT_USE").encode()
+        self.key = _require_fernet_key()
         self.fernet = Fernet(self.key)
     # [/DEF:EncryptionManager.__init__:Function]
 
@@ -97,7 +114,7 @@ class LLMProviderService:
     # @PURPOSE: Creates a new LLM provider with encrypted API key.
     # @PRE: config must contain valid provider configuration.
     # @POST: New provider created and persisted to database.
-    def create_provider(self, config: LLMProviderConfig) -> LLMProvider:
+    def create_provider(self, config: "LLMProviderConfig") -> LLMProvider:
         with belief_scope("create_provider"):
             encrypted_key = self.encryption.encrypt(config.api_key)
             db_provider = LLMProvider(
@@ -119,7 +136,7 @@ class LLMProviderService:
     # @PURPOSE: Updates an existing LLM provider.
     # @PRE: provider_id must exist, config must be valid.
     # @POST: Provider updated and persisted to database.
-    def update_provider(self, provider_id: str, config: LLMProviderConfig) -> Optional[LLMProvider]:
+    def update_provider(self, provider_id: str, config: "LLMProviderConfig") -> Optional[LLMProvider]:
         with belief_scope("update_provider"):
             db_provider = self.get_provider(provider_id)
             if not db_provider:
@@ -180,4 +197,4 @@ class LLMProviderService:
 
 # [/DEF:LLMProviderService:Class]
 
-# [/DEF:backend.src.services.llm_provider:Module]
+# [/DEF:backend.src.services.llm_provider:Module]