openssl-encrypt 1.3.0

A package for secure file encryption and decryption based on modern ciphers using heavy-compute-load chaining of hashing and KDF to generate strong encryption password based on users provided password to ensure secure encryption of files

OpenSSL Encrypt

A Python-based file encryption tool with modern ciphers, post-quantum algorithms, and defense-in-depth key derivation.

History

The project is historically named openssl-encrypt because it once was a Python script wrapper around OpenSSL. That approach stopped working with recent Python versions, so I did a complete rewrite in pure Python using modern ciphers and hashes. The project name is a “homage” to its roots.

What’s New in v1.3.0

Version 1.3.0 focuses on security hardening, testing capabilities, and advanced features:

• Testing: Comprehensive test suite (crypt test) with fuzzing, side-channel analysis, and benchmarking
• Security: O_NOFOLLOW symlink attack prevention in D-Bus service, audit logging, debug mode warnings
• Features: Steganography support, enhanced plugin system with process isolation, improved RandomX KDF
• Quality: 8.8/10 security score (independent review), 950+ tests, zero vulnerable dependencies

Security Architecture

Chained Key Derivation

This tool uses a chained hash/KDF architecture where each round’s output determines the next round’s salt:

Password + Salt₀ → KDF₁ → Result₁ → Salt₁ = f(Result₁) → KDF₂ → Result₂ → ... → Final Key

Design Properties:

• Sequential Dependency: Each round requires the previous round’s result
• Dynamic Salting: Salts are derived from previous outputs, not predictable in advance
• Memory-Hard Functions: Argon2 and Balloon hashing require significant memory per attempt

Attack Resistance

The chained architecture provides several security properties:

Attack Vector	Mitigation
GPU/ASIC parallelization	Sequential dependency forces single-threaded computation
Rainbow tables	Dynamic per-round salts prevent precomputation
Time-memory trade-offs	Cannot cache intermediate results across attempts
Quantum key recovery	Hybrid PQC modes (ML-KEM, HQC) for key encapsulation

Computational Cost Estimates

Password Entropy	KDF Configuration	Time/Attempt	Brute-Force Estimate*
50 bits (8 random chars)	Balloon ×5	~40s	~10²² years
60 bits (10 random chars)	Balloon ×5	~40s	~10²⁵ years
80 bits (13 random chars)	Balloon ×5	~40s	~10³¹ years

*Estimates assume: 95-character set, uniformly random password, single-threaded attack, no implementation flaws. Actual security depends on password quality and operational security.

Security Considerations

• Strong passwords (12+ random characters) make brute-force computationally infeasible
• Sequential chaining prevents parallelization of key derivation
• Post-quantum algorithms provide resistance against quantum key-recovery attacks
• Limitations: Implementation bugs, side-channel attacks, weak passwords, or compromised systems remain potential risks. No cryptographic system provides absolute guarantees.

Security Review

The v1.3.0 codebase received an independent security review:

• Score: 8.8/10
• Critical/High findings: 0
• Medium findings: 3 (defense-in-depth improvements, not blocking)
• Dependencies: pip-audit clean, zero known vulnerabilities

See <SECURITY_REVIEW_v1.3.0.md> for the full report.

Features

Symmetric Encryption

Modern AEAD (Authenticated Encryption with Associated Data) ciphers:

Algorithm	Status	Notes
AES-GCM	✅ Recommended	NIST standard, hardware-accelerated
AES-GCM-SIV	✅ Recommended	Nonce-misuse resistant
ChaCha20-Poly1305	✅ Recommended	Software-optimized, constant-time
XChaCha20-Poly1305	✅ Recommended	Extended nonce (192-bit)
AES-SIV	✅ Supported	Deterministic encryption
Fernet	✅ Default	AES-128-CBC + HMAC, simple API
AES-OCB3	⚠️ Decrypt only	Deprecated in v1.2.0
Camellia	⚠️ Decrypt only	Deprecated in v1.2.0

Post-Quantum Cryptography

Hybrid encryption combining classical symmetric ciphers with post-quantum KEMs:

NIST Standardized:

• ML-KEM (FIPS 203): ML-KEM-512, ML-KEM-768, ML-KEM-1024
• Kyber: Kyber-512, Kyber-768, Kyber-1024 (original implementation)

NIST Selected (2025):

• HQC: HQC-128, HQC-192, HQC-256

Signature Schemes (for authenticated encryption):

• MAYO: MAYO-1, MAYO-2, MAYO-3, MAYO-5
• CROSS: CROSS-R-SDPG-1, CROSS-R-SDPG-3, CROSS-R-SDPG-5

Key Derivation Functions

KDF	Type	Status	Use Case
Argon2id	Memory-hard	✅ Recommended	Default for password hashing
Balloon	Memory-hard	✅ Recommended	Alternative to Argon2
Scrypt	Memory-hard	✅ Supported	GPU-resistant
HKDF	Extract-and-expand	✅ Supported	Key expansion
RandomX	CPU-hard	✅ Supported	Anti-ASIC (from Monero)
PBKDF2	Iterative	⚠️ Decrypt only	Deprecated in v1.2.0

Hash Functions

For key derivation chaining:

• SHA-2 Family (FIPS 180-4): SHA-512, SHA-384, SHA-256, SHA-224
• SHA-3 Family (FIPS 202): SHA3-512, SHA3-384, SHA3-256, SHA3-224
• BLAKE Family: BLAKE2b, BLAKE3
• SHAKE (XOF): SHAKE-256, SHAKE-128
• Legacy: Whirlpool (decrypt only in v1.2.0+)

Additional Security Features

Memory Protection:

• Secure memory allocation with mlock/VirtualLock
• Multi-pass memory wiping (random, 0xFF, 0xAA, 0x55, 0x00)
• Constant-time operations for timing attack resistance

File Operations:

• Multi-pass secure deletion (configurable passes)
• Atomic file operations
• Symlink attack protection (O_NOFOLLOW in D-Bus service)

Key Management:

• Encrypted keystore for PQC keys
• Key rotation support
• Dual encryption (password + keystore)

Operational:

• Password policy enforcement
• Common password dictionary check
• Audit logging

Installation

Flatpak (Recommended)

The easiest way to install with all dependencies included (Python, liboqs, liboqs-python, Flutter GUI):

# Add the repository
flatpak remote-add --if-not-exists openssl-encrypt https://flatpak.rm-rf.ch/openssl-encrypt.flatpakrepo

# Install latest stable version
flatpak install openssl-encrypt com.opensslencrypt.OpenSSLEncrypt

# Run the application
flatpak run com.opensslencrypt.OpenSSLEncrypt --help

Benefits:

• All dependencies pre-installed (including liboqs and Python bindings)
• Flutter Desktop GUI included
• Sandboxed environment
• Automatic updates
• Works on any Linux distribution

Build Flatpak locally (alternative to using the repository):

# Clone the repository
git clone https://github.com/jahlives/openssl_encrypt.git
cd openssl_encrypt/flatpak

# Build and install locally (includes Flutter GUI)
./build-flatpak.sh --build-flutter --local-install

# Or install as development branch (recommended for testing, runs parallel to stable)
./build-flatpak.sh --build-flutter --dev-install

# Run the locally installed flatpak
flatpak run com.opensslencrypt.OpenSSLEncrypt

Build options:

• --build-flutter - Build Flutter Desktop GUI before packaging
• --local-install - Install as stable branch (overwrites production)
• --dev-install - Install as development branch (parallel to production, recommended)
• -f, --force - Force clean build cache

See flatpak/README.md for detailed build instructions.

PyPI / Source Installation

Requirements:

• Python 3.11+ (3.12 or 3.13 recommended)

Core Dependencies:

cryptography>=44.0.1
argon2-cffi>=23.1.0
PyYAML>=6.0.2
blake3>=1.0.0

Optional Dependencies:

liboqs-python          # Extended PQC support (HQC, ML-DSA, etc.)
                       # Requires liboqs (https://github.com/open-quantum-safe/liboqs)
tkinter                # GUI (usually included with Python)

Install:

# From PyPI (when available)
pip install openssl-encrypt

# From source
git clone https://github.com/jahlives/openssl_encrypt.git
cd openssl_encrypt
pip install -e .

Note: For full post-quantum support (HQC, ML-DSA), you need to manually install liboqs and liboqs-python. The Flatpak version includes these by default.

Usage

Command-Line Interface

# Basic encryption (Fernet, default settings)
python -m openssl_encrypt.crypt encrypt -i file.txt -o file.txt.enc

# AES-GCM with Argon2
python -m openssl_encrypt.crypt encrypt -i file.txt -o file.txt.enc \
    --algorithm aes-gcm \
    --enable-argon2 --argon2-rounds 3

# Post-quantum hybrid encryption
python -m openssl_encrypt.crypt encrypt -i file.txt -o file.txt.enc \
    --algorithm ml-kem-768-hybrid

# Using security templates
python -m openssl_encrypt.crypt encrypt -i file.txt --quick      # Fast, good security
python -m openssl_encrypt.crypt encrypt -i file.txt --standard   # Balanced (default)
python -m openssl_encrypt.crypt encrypt -i file.txt --paranoid   # Maximum security

# Decryption (algorithm auto-detected from metadata)
python -m openssl_encrypt.crypt decrypt -i file.txt.enc -o file.txt

# Secure file deletion
python -m openssl_encrypt.crypt shred -i sensitive.txt --passes 3

# Generate random password
python -m openssl_encrypt.crypt generate --length 20

Graphical User Interface

python -m openssl_encrypt.crypt_gui
# or
python -m openssl_encrypt.cli --gui

Flutter Desktop GUI

Cross-platform GUI available for Linux, macOS, and Windows. See the User Guide for installation.

Keystore Operations

# Create keystore
python -m openssl_encrypt.keystore_cli_main create --keystore-path keys.pqc

# Generate PQC keypair
python -m openssl_encrypt.keystore_cli_main generate --keystore-path keys.pqc \
    --algorithm ml-kem-768

# Encrypt with keystore
python -m openssl_encrypt.crypt encrypt -i file.txt \
    --keystore keys.pqc --key-id my-key

Configuration Templates

Pre-configured security profiles in templates/:

Template	Use Case	KDF	Rounds	Time
quick.json	Fast encryption, good security	Argon2	1	~1s
standard.json	Balanced (default)	Argon2 + SHA3	3	~5s
paranoid.json	Maximum security	Argon2 + Balloon + SHA3	10+	~60s+

Project Structure

openssl_encrypt/
├── crypt.py                 # CLI entry point
├── crypt_gui.py             # Tkinter GUI
├── modules/
│   ├── crypt_core.py        # Core encryption/decryption
│   ├── crypt_cli.py         # CLI implementation
│   ├── crypt_utils.py       # Utilities (shred, password gen)
│   ├── crypt_errors.py      # Exception classes
│   ├── secure_memory.py     # Memory protection
│   ├── secure_ops.py        # Constant-time operations
│   ├── balloon.py           # Balloon hashing
│   ├── randomx.py           # RandomX KDF
│   ├── pqc.py               # Post-quantum crypto
│   ├── pqc_adapter.py       # PQC algorithm adapter
│   ├── keystore_cli.py      # Keystore management
│   ├── password_policy.py   # Password validation
│   ├── dbus_service.py      # D-Bus integration (Linux)
│   └── plugin_system/       # Plugin sandbox
├── unittests/
│   ├── unittests.py         # Main test suite (950+ tests)
│   └── testfiles/           # Test vectors (password: 1234)
├── templates/               # Security profiles
└── docs/                    # Documentation

Documentation

Document	Description
User Guide	Installation, usage, examples, troubleshooting
Keystore Guide	PQC key management, dual encryption
Security Documentation	Architecture, threat model, best practices
Algorithm Reference	Cipher and KDF specifications
Metadata Formats	File format specs (v3, v4, v5)
Development Setup	Contributing, CI/CD, testing

Testing

# Run all tests
pytest openssl_encrypt/unittests/

# Run with coverage
pytest --cov=openssl_encrypt openssl_encrypt/unittests/

# Run specific test class
pytest openssl_encrypt/unittests/unittests.py::TestCryptCore

Test files in unittests/testfiles/ are encrypted with password 1234.

Support

• Issues: GitHub Issues
• Email: [e-mail]
• Security vulnerabilities: Email only (not public issues)

License

See file.

---

OpenSSL Encrypt – File encryption with modern ciphers, post-quantum algorithms, and defense-in-depth key derivation.