security: implement CRYPTO-001 and TIMING-001 remediations

CRYPTO-001: Certificate serial collision detection
- Add _generate_unique_serial() helper for database-backed PKI
- Add _generate_unique_serial() method for in-memory PKI class
- Check database for existing serial before certificate issuance
- Retry with new random serial if collision detected (max 5 attempts)

TIMING-001: Constant-time database lookups for sensitive queries
- Add dummy PBKDF2 verification when paste not found
- Prevents timing-based enumeration (attackers can't distinguish
  'not found' from 'wrong password' by measuring response time)

PENTEST_PLAN.md

@@ -259,8 +259,8 @@ Testing uses specialized Claude subagents for different security domains, with f
 
 ### Long-term (Low)
 
-- [ ] **CRYPTO-001**: Add certificate serial collision detection
-- [ ] **TIMING-001**: Add constant-time database lookups for sensitive queries
+- [x] **CRYPTO-001**: Add certificate serial collision detection
+- [x] **TIMING-001**: Add constant-time database lookups for sensitive queries
 
 ---
 

app/api/routes.py

@@ -485,6 +485,16 @@ def fetch_paste(paste_id: str, check_password: bool = True) -> Response | None:
     ).fetchone()
 
     if row is None:
+        # TIMING-001: Perform dummy password verification to prevent timing-based
+        # enumeration (attacker can't distinguish "not found" from "wrong password"
+        # by measuring response time)
+        if check_password:
+            dummy_hash = (
+                "$pbkdf2-sha256$600000$"
+                "0000000000000000000000000000000000000000000000000000000000000000$"
+                "0000000000000000000000000000000000000000000000000000000000000000"
+            )
+            verify_password("dummy", dummy_hash)
         db.commit()
         return error_response("Paste not found", 404)
 

app/pki.py

@@ -43,6 +43,7 @@ except ImportError:
 _KDF_ITERATIONS = 600000  # OWASP 2023 recommendation
 _SALT_LENGTH = 32
 _KEY_LENGTH = 32  # AES-256
+_SERIAL_MAX_RETRIES = 5  # CRYPTO-001: Max attempts for unique serial generation
 
 
 class PKIError(Exception):
@@ -264,6 +265,29 @@ class PKI:
         """Check if CA exists."""
         return self._ca_store is not None
 
+    def _generate_unique_serial(self) -> int:
+        """Generate a unique certificate serial number.
+
+        CRYPTO-001: Checks existing certificates for collision.
+
+        Returns:
+            Unique serial number as integer
+
+        Raises:
+            PKIError: If unable to generate unique serial after max retries
+        """
+        existing_serials = {
+            cert["serial"] for cert in self._certificates.values()
+        }
+
+        for _ in range(_SERIAL_MAX_RETRIES):
+            serial = x509.random_serial_number()
+            serial_hex = format(serial, "032x")
+            if serial_hex not in existing_serials:
+                return serial
+
+        raise PKIError("Failed to generate unique serial after max retries")
+
     def generate_ca(
         self,
         common_name: str,
@@ -524,7 +548,8 @@ class PKI:
 
         # Build certificate
         now = datetime.now(UTC)
-        serial = x509.random_serial_number()
+        # CRYPTO-001: Use collision-safe serial generation
+        serial = self._generate_unique_serial()
 
         subject = x509.Name(
             [
@@ -784,6 +809,37 @@ def get_ca_info(skip_enabled_check: bool = False) -> dict | None:
     }
 
 
+def _generate_unique_serial(db: Any) -> int:
+    """Generate a unique certificate serial number.
+
+    CRYPTO-001: Checks database for collision before returning.
+
+    Args:
+        db: Database connection
+
+    Returns:
+        Unique serial number as integer
+
+    Raises:
+        PKIError: If unable to generate unique serial after max retries
+    """
+    _require_crypto()
+
+    for _ in range(_SERIAL_MAX_RETRIES):
+        serial = x509.random_serial_number()
+        serial_hex = format(serial, "032x")
+
+        # Check for collision
+        existing = db.execute(
+            "SELECT 1 FROM issued_certificates WHERE serial = ?", (serial_hex,)
+        ).fetchone()
+
+        if existing is None:
+            return serial
+
+    raise PKIError("Failed to generate unique serial after max retries")
+
+
 def generate_ca(
     common_name: str,
     password: str,
@@ -958,7 +1014,8 @@ def issue_certificate(
 
     # Build certificate
     now = datetime.now(UTC)
-    serial = x509.random_serial_number()
+    # CRYPTO-001: Use collision-safe serial generation
+    serial = _generate_unique_serial(db)
 
     subject = x509.Name(
         [

tests/test_cli_security.py

@@ -43,8 +43,8 @@ class TestClipboardPathValidation:
     def test_untrusted_unix_paths(self, fpaste):
         """Paths in user-writable directories should be rejected."""
         assert fpaste.is_trusted_clipboard_path("/home/user/bin/xclip") is False
-        assert fpaste.is_trusted_clipboard_path("/tmp/xclip") is False
-        assert fpaste.is_trusted_clipboard_path("/var/tmp/malicious") is False
+        assert fpaste.is_trusted_clipboard_path("/tmp/xclip") is False  # noqa: S108
+        assert fpaste.is_trusted_clipboard_path("/var/tmp/malicious") is False  # noqa: S108
         assert fpaste.is_trusted_clipboard_path("./xclip") is False
         assert fpaste.is_trusted_clipboard_path("") is False
 
@@ -70,7 +70,7 @@ class TestClipboardPathValidation:
         """find_clipboard_command should reject tools in untrusted paths."""
         with patch("shutil.which") as mock_which:
             # Untrusted path should be rejected
-            mock_which.return_value = "/tmp/malicious/xclip"
+            mock_which.return_value = "/tmp/malicious/xclip"  # noqa: S108
             result = fpaste.find_clipboard_command(fpaste.CLIPBOARD_READ_COMMANDS)
             assert result is None