Encryption Skill

name: encryption version: 1.0.0 domain: security/cryptography risk_level: HIGH languages: [python, typescript, rust, go] frameworks: [sqlcipher, cryptography, libsodium] requires_security_review: true compliance: [GDPR, HIPAA, PCI-DSS, SOC2] last_updated: 2025-01-15

MANDATORY READING PROTOCOL: Before implementing ANY encryption, read

references/advanced-patterns.md

for key derivation and

references/security-examples.md

for implementation patterns.

1. Overview

1.1 Purpose and Scope

This skill provides secure-by-default patterns for implementing encryption in JARVIS AI Assistant, covering:

• SQLCipher: Encrypted SQLite database with AES-256-GCM
• Argon2id: Memory-hard key derivation function
• Key Management: Secure generation, storage, rotation, and destruction
• Secure Memory: Protection against memory disclosure attacks

1.2 Risk Assessment

Risk Level: HIGH

Justification:

• Cryptographic failures expose all protected data
• Key compromise leads to complete confidentiality loss
• Implementation errors are catastrophic and often undetectable
• Regulatory violations (GDPR, HIPAA, PCI-DSS) carry severe penalties

Attack Surface:

• Key derivation weaknesses
• Insecure random number generation
• Timing side-channels
• Memory disclosure (cold boot, crash dumps)
• Key reuse across contexts

2. Core Responsibilities

2.1 Primary Functions

1. Encrypt data at rest using AES-256-GCM with authenticated encryption
2. Derive keys securely using Argon2id with appropriate parameters
3. Manage key lifecycle including rotation, escrow, and destruction
4. Protect key material in memory and during operations
5. Integrate with OS keychains for master key storage

2.2 Core Principles

1. TDD First - Write tests before implementation; test encryption/decryption round-trips, authentication failures, and edge cases
2. Performance Aware - Cache derived keys, use streaming for large data, leverage hardware acceleration
3. Security by Default - Use authenticated encryption modes, memory-hard KDFs, secure random sources
4. Defense in Depth - Multiple layers of protection, fail securely, minimize key exposure

2.3 Security Principles

• NEVER implement custom cryptographic algorithms
• NEVER use ECB mode or unauthenticated encryption
• ALWAYS use cryptographically secure random number generators
• ALWAYS validate ciphertext authenticity before decryption
• ALWAYS use constant-time comparison for authentication tags

3. Implementation Workflow (TDD)

Step 1: Write Failing Test First

import pytest
from cryptography.exceptions import InvalidTag

class TestEncryptionTDD:
    """TDD tests for encryption implementation."""

    def test_encrypt_decrypt_roundtrip(self):
        """Test that encryption followed by decryption returns original data."""
        from jarvis.security.encryption import SecureEncryption

        key = secrets.token_bytes(32)
        encryptor = SecureEncryption(key)

        plaintext = b"sensitive data for JARVIS"
        ciphertext = encryptor.encrypt(plaintext)
        decrypted = encryptor.decrypt(ciphertext)

        assert decrypted == plaintext
        assert ciphertext != plaintext  # Must be encrypted

    def test_tampered_ciphertext_raises_error(self):
        """Test that tampered ciphertext is rejected."""
        from jarvis.security.encryption import SecureEncryption

        key = secrets.token_bytes(32)
        encryptor = SecureEncryption(key)

        ciphertext = encryptor.encrypt(b"secret")
        tampered = ciphertext[:-1] + bytes([ciphertext[-1] ^ 0xFF])

        with pytest.raises(InvalidTag):
            encryptor.decrypt(tampered)

    def test_key_derivation_consistency(self):
        """Same password + salt = same key; different salt = different key."""
        from jarvis.security.encryption import SecureKeyDerivation
        password = "strong_password_123"
        salt = secrets.token_bytes(16)
        key1, _ = SecureKeyDerivation.derive_key(password, salt)
        key2, _ = SecureKeyDerivation.derive_key(password, salt)
        assert key1 == key2 and len(key1) == 32

        key3, salt3 = SecureKeyDerivation.derive_key(password)
        assert key1 != key3  # Different salt = different key

Step 2: Implement Minimum to Pass

Implement only what's needed to pass the tests. Start with basic encryption/decryption, then add key derivation.

Step 3: Refactor Following Patterns

After tests pass, add: memory protection, error handling, AAD support, key caching.

Step 4: Run Full Verification

# Run encryption tests with coverage
pytest tests/security/test_encryption.py -v --cov=jarvis.security.encryption --cov-fail-under=90

# Run security-specific tests
pytest tests/security/ -k "encryption or crypto" -v

# Check for timing vulnerabilities
pytest tests/security/test_timing.py -v

# Verify no secrets in output
pytest --log-cli-level=DEBUG 2>&1 | grep -i "key\|secret\|password" && echo "WARNING: Secrets in logs!"

4. Technology Stack

4.1 Recommended Libraries

cryptography

argon2-cffi

@noble/ciphers

ring

crypto/cipher

golang.org/x/crypto

4.2 SQLCipher Configuration

Minimum Version: SQLCipher 4.5.6+ (includes SQLite 3.44.2)

# SQLCipher secure configuration
SQLCIPHER_PRAGMAS = {
    'key': None,  # Set via secure key injection
    'cipher': 'aes-256-gcm',
    'kdf_iter': 256000,  # PBKDF2 iterations
    'cipher_page_size': 4096,
    'cipher_kdf_algorithm': 'PBKDF2_HMAC_SHA512',
    'cipher_hmac_algorithm': 'HMAC_SHA512',
    'cipher_plaintext_header_size': 0,
}

5. Performance Patterns

5.1 Key Caching

Bad: Deriving key on every operation (~500ms per Argon2id call)

Good - Cache with TTL:

class CachedKeyManager:
    def __init__(self, cache_ttl: int = 300):
        self._cache: dict[str, tuple[bytes, float]] = {}
        self._ttl = cache_ttl

    def get_key(self, password: str, salt: bytes) -> bytes:
        cache_key = f"{hash(password)}:{salt.hex()}"
        if cache_key in self._cache:
            key, ts = self._cache[cache_key]
            if time.time() - ts < self._ttl:
                return key
        key, _ = SecureKeyDerivation.derive_key(password, salt)
        self._cache[cache_key] = (key, time.time())
        return key

5.2 Streaming Encryption for Large Data

Bad:

data = f.read()

Good - Stream with chunking (64KB chunks):

nonce = secrets.token_bytes(12)
encryptor = Cipher(algorithms.AES(key), modes.GCM(nonce)).encryptor()
with open(input_path, 'rb') as fin, open(output_path, 'wb') as fout:
    fout.write(nonce)
    while chunk := fin.read(64 * 1024):
        fout.write(encryptor.update(chunk))
    fout.write(encryptor.finalize() + encryptor.tag)

5.3 Hardware Acceleration

Bad: PyCryptodome without OpenSSL backend (10-100x slower)

Good: Use

cryptography

5.4 Batch Operations

Bad - Individual loop with append:

results = []
for record in records:
    results.append(encryptor.encrypt(record))

Good - List comprehension with single encryptor:

encryptor = SecureEncryption(key)
results = [encryptor.encrypt(record) for record in records]

# For large batches, use ProcessPoolExecutor for parallelization

5.5 Memory-Safe Key Handling

Bad - Keys remain in memory:

self.key = SecureKeyDerivation.derive_key(password)  # Never cleared

Good - Zero keys after use with context manager:

import ctypes

class SecureKeyHolder:
    def __init__(self, password: str):
        self._key, self.salt = SecureKeyDerivation.derive_key(password)

    def __exit__(self, *args):
        if self._key:
            key_buffer = (ctypes.c_char * len(self._key)).from_buffer_copy(self._key)
            ctypes.memset(key_buffer, 0, len(self._key))
            self._key = None

# Usage: with SecureKeyHolder(password) as kh: encrypt(kh._key, data)

6. Implementation Patterns

6.1 Key Derivation with Argon2id

from argon2 import PasswordHasher
from argon2.low_level import hash_secret_raw, Type
import secrets

class SecureKeyDerivation:
    """Derive encryption keys from passwords using Argon2id."""

    # OWASP recommended parameters for sensitive data
    TIME_COST = 3        # Iterations
    MEMORY_COST = 65536  # 64 MiB
    PARALLELISM = 4      # Threads
    HASH_LEN = 32        # 256 bits for AES-256
    SALT_LEN = 16        # 128 bits minimum

    @classmethod
    def derive_key(cls, password: str, salt: bytes = None) -> tuple[bytes, bytes]:
        """
        Derive a 256-bit key from password.

        Returns:
            tuple: (derived_key, salt) for storage
        """
        if salt is None:
            salt = secrets.token_bytes(cls.SALT_LEN)

        # Validate inputs
        if not password or len(password) < 12:
            raise ValueError("Password must be at least 12 characters")

        key = hash_secret_raw(
            secret=password.encode('utf-8'),
            salt=salt,
            time_cost=cls.TIME_COST,
            memory_cost=cls.MEMORY_COST,
            parallelism=cls.PARALLELISM,
            hash_len=cls.HASH_LEN,
            type=Type.ID  # Argon2id
        )

        return key, salt

6.2 AES-256-GCM Encryption

from cryptography.hazmat.primitives.ciphers.aead import AESGCM
import secrets

class SecureEncryption:
    """AES-256-GCM authenticated encryption."""

    NONCE_SIZE = 12  # 96 bits recommended for GCM
    KEY_SIZE = 32    # 256 bits

    def __init__(self, key: bytes):
        if len(key) != self.KEY_SIZE:
            raise ValueError(f"Key must be {self.KEY_SIZE} bytes")
        self._aesgcm = AESGCM(key)

    def encrypt(self, plaintext: bytes, associated_data: bytes = None) -> bytes:
        """
        Encrypt with random nonce, prepended to ciphertext.

        Returns:
            bytes: nonce || ciphertext || tag
        """
        nonce = secrets.token_bytes(self.NONCE_SIZE)
        ciphertext = self._aesgcm.encrypt(nonce, plaintext, associated_data)
        return nonce + ciphertext

    def decrypt(self, ciphertext: bytes, associated_data: bytes = None) -> bytes:
        """
        Decrypt and verify authenticity.

        Raises:
            InvalidTag: If authentication fails
        """
        if len(ciphertext) < self.NONCE_SIZE + 16:  # nonce + tag minimum
            raise ValueError("Ciphertext too short")

        nonce = ciphertext[:self.NONCE_SIZE]
        actual_ciphertext = ciphertext[self.NONCE_SIZE:]

        return self._aesgcm.decrypt(nonce, actual_ciphertext, associated_data)

6.3 SQLCipher Database Integration

import sqlcipher3
from contextlib import contextmanager

class EncryptedDatabase:
    """Encrypted SQLite database using SQLCipher."""

    def __init__(self, db_path: str, key: bytes):
        self._db_path = db_path
        self._key = key
        self._conn = None

    @contextmanager
    def connect(self):
        """Context manager for database connections."""
        conn = sqlcipher3.connect(self._db_path)
        try:
            # Apply security pragmas
            conn.execute(f"PRAGMA key = \"x'{self._key.hex()}'\";")
            conn.execute("PRAGMA cipher = 'aes-256-gcm';")
            conn.execute("PRAGMA kdf_iter = 256000;")
            conn.execute("PRAGMA cipher_page_size = 4096;")

            # Verify encryption is active
            result = conn.execute("PRAGMA cipher_version;").fetchone()
            if not result:
                raise RuntimeError("SQLCipher encryption not active")

            yield conn
            conn.commit()
        except Exception:
            conn.rollback()
            raise
        finally:
            conn.close()

    def rekey(self, new_key: bytes):
        """Rotate database encryption key."""
        with self.connect() as conn:
            conn.execute(f"PRAGMA rekey = \"x'{new_key.hex()}'\";")
        self._key = new_key

7. Security Standards

7.1 Known Vulnerabilities

7.2 OWASP Mapping

7.3 Cryptography Standards

Approved Algorithms:

• Symmetric: AES-256-GCM (primary), ChaCha20-Poly1305 (alternative)
• KDF: Argon2id (primary), PBKDF2-HMAC-SHA512 (SQLCipher)
• Hash: SHA-256, SHA-512, BLAKE2b
• RNG: OS CSPRNG only (

  secrets

  module,

  /dev/urandom

  )

Prohibited:

• DES, 3DES, RC4, Blowfish
• MD5, SHA-1 for security purposes
• ECB mode for any cipher
• Custom random number generators

8. Testing Requirements

See Section 3 (Implementation Workflow - TDD) for comprehensive test examples including:

• Encryption/decryption round-trips
• Ciphertext tampering detection
• Key derivation consistency
• Nonce uniqueness validation

9. Common Mistakes

9.1 Critical Anti-Patterns

modes.ECB()

AESGCM(key)

SECRET_KEY = b"..."

os_keychain.get_key()

struct.pack(">Q", time())

secrets.token_bytes(12)

modes.CBC(iv)

aesgcm.encrypt(nonce, pt, aad)

sha256(password)

Argon2id.derive_key()

10. Pre-Implementation Checklist

Phase 1: Before Writing Code

• Read threat model in

  references/threat-model.md

• Identify data classification (PII, PHI, credentials)
• Choose appropriate algorithm (AES-256-GCM or ChaCha20-Poly1305)
• Design key derivation strategy (Argon2id parameters)
• Plan key storage (OS keychain integration)
• Write failing tests for encrypt/decrypt round-trips
• Write tests for authentication tag verification
• Write tests for key derivation consistency

Phase 2: During Implementation

• Use

  cryptography

  library (not custom implementations)
• Generate nonces with

  secrets.token_bytes(12)

• Implement key caching with TTL for performance
• Use streaming for files >10MB
• Zero key material after use (SecureKeyHolder pattern)
• Add associated data (AAD) for context binding
• Handle InvalidTag exceptions without leaking info
• Run tests after each function implementation

Phase 3: Before Committing

• All TDD tests pass with 90%+ coverage
• Nonce uniqueness validated over 10,000+ operations
• Key derivation timing variance <10%
• No secrets in logs (

  grep -i "key\|secret\|password"

  )
• Dependency scanning clean (no CVEs)
• Performance benchmarks meet targets:
  • Key derivation: <1s
  • Encryption: >100MB/s
  • Batch operations: Linear scaling
• Security review requested for HIGH risk code

11. Summary

Key Objectives: AES-256-GCM with random nonces, Argon2id KDF, OS keychain integration, authenticated encryption, key rotation support.

Security Reminders: No custom crypto, use audited libraries, test auth tags, rotate keys on schedule.

References:

references/advanced-patterns.md

references/security-examples.md

references/threat-model.md

Encryption done wrong is worse than no encryption - it provides false confidence.