team-tryouts/app/supporting_scripts/security_scan.py

"""Security validation script for the Team Tryouts application.

This script performs pre-deployment security checks to validate:
- HTTP security headers
- Cookie security attributes
- Debug mode status
- HTTPS configuration
- Dependency vulnerabilities
- Database connectivity

Usage:
    python security_scan.py [--url http://localhost:5000]
"""

import os
import sys
import json
import subprocess
import urllib.request
import ssl
from datetime import datetime


def check_environment():
    """Check required environment variables are set.

    Returns:
        bool: True if all critical variables are set.
    """
    print('=' * 60)
    print('1. ENVIRONMENT VARIABLES CHECK')
    print('=' * 60)

    critical_vars = ['SECRET_KEY']
    recommended_vars = ['DATABASE_URL', 'CORS_ALLOWED_ORIGINS']
    all_ok = True

    for var in critical_vars:
        value = os.getenv(var)
        if value:
            # Check SECRET_KEY is not a default/weak value
            if var == 'SECRET_KEY' and len(value) < 32:
                print(f'[WARN] {var} is set but too short (less than 32 chars)')
                all_ok = False
            else:
                print(f'[OK] {var} is set')
        else:
            print(f'[FAIL] {var} is not set!')
            all_ok = False

    for var in recommended_vars:
        value = os.getenv(var)
        if value:
            print(f'[OK] {var} is set')
        else:
            print(f'[INFO] {var} is not set (using default)')

    # Check FLASK_DEBUG
    debug = os.getenv('FLASK_DEBUG', 'false').lower()
    if debug == 'true':
        print('[WARN] FLASK_DEBUG is enabled! Should be disabled in production.')
    else:
        print('[OK] FLASK_DEBUG is disabled')

    return all_ok


def check_https_headers(url):
    """Check HTTP security headers from a running application.

    Args:
        url: The base URL of the application to check.

    Returns:
        bool: True if all critical headers are present.
    """
    print('\n' + '=' * 60)
    print('2. HTTP SECURITY HEADERS CHECK')
    print('=' * 60)

    required_headers = {
        'Strict-Transport-Security': 'HSTS enabled',
        'X-Content-Type-Options': 'Prevents MIME sniffing',
        'X-Frame-Options': 'Prevents clickjacking',
        'Content-Security-Policy': 'CSP configured',
        'Referrer-Policy': 'Referrer control',
        'Permissions-Policy': 'Permissions control',
        'Cross-Origin-Opener-Policy': 'Cross-origin isolation',
    }

    all_ok = True

    try:
        # Create a context that doesn't verify SSL (for local testing)
        ctx = ssl.create_default_context()
        ctx.check_hostname = False
        ctx.verify_mode = ssl.CERT_NONE

        req = urllib.request.Request(url, method='HEAD')

        try:
            with urllib.request.urlopen(req, context=ctx, timeout=10) as response:
                headers = response.headers
                status = response.status

                print(f'[INFO] Response status: {status}')

                for header, description in required_headers.items():
                    if header in headers:
                        print(f'[OK] {header}: {description}')
                    else:
                        print(f'[FAIL] {header} is missing: {description}')
                        all_ok = False

                # Check cookie attributes if any set-cookie headers exist
                if 'Set-Cookie' in headers:
                    cookie = headers['Set-Cookie']
                    if 'Secure' in cookie:
                        print('[OK] Cookies have Secure flag')
                    else:
                        print('[WARN] Cookies missing Secure flag')
                        all_ok = False

                    if 'HttpOnly' in cookie:
                        print('[OK] Cookies have HttpOnly flag')
                    else:
                        print('[WARN] Cookies missing HttpOnly flag')
                        all_ok = False

                    if 'SameSite' in cookie:
                        print(
                            f'[OK] Cookies have SameSite={cookie.split("SameSite=")[1].split(";")[0] if "SameSite=" in cookie else "?"}'
                        )
                    else:
                        print('[WARN] Cookies missing SameSite attribute')
                        all_ok = False
                else:
                    print('[INFO] No Set-Cookie headers in response')

        except urllib.error.HTTPError as e:
            print(f'[INFO] Got HTTP {e.code} (may need authentication)')
            # Still check headers even on error responses
            for header, description in required_headers.items():
                if header in e.headers:
                    print(f'[OK] {header}: {description}')
                else:
                    print(f'[FAIL] {header} is missing: {description}')
                    all_ok = False

    except urllib.error.URLError as e:
        print(f'[SKIP] Cannot connect to {url}: {e.reason}')
        print('[SKIP] Run with --url <application_url> to check headers')
        return True  # Not a failure, just can't check

    return all_ok


def check_dependencies():
    """Run pip-audit to check for known vulnerabilities.

    Returns:
        bool: True if no critical vulnerabilities found.
    """
    print('\n' + '=' * 60)
    print('3. DEPENDENCY VULNERABILITY SCAN')
    print('=' * 60)

    try:
        result = subprocess.run(
            [sys.executable, '-m', 'pip_audit', '--format', 'json'],
            capture_output=True,
            text=True,
            timeout=60,
        )

        if result.returncode == 0:
            print('[OK] No known vulnerabilities found')
            return True
        try:
            data = json.loads(result.stdout)
            # pip-audit's "dependencies" array lists EVERY dependency, each
            # carrying a "vulns" list that is empty when the package is
            # clean. Treating the array itself as the vulnerability list
            # reported all ~45 installed packages as vulnerable on every
            # run, which is why this check was pure noise.
            affected = [dep for dep in data.get('dependencies', []) if dep.get('vulns')]
            if affected:
                for dep in affected:
                    ids = ', '.join(v.get('id', '?') for v in dep.get('vulns', []))
                    print(f'[FAIL] {dep["name"]}=={dep["version"]}: {ids}')
                return False
            print('[OK] No vulnerabilities found')
            return True
        except json.JSONDecodeError:
            if result.stdout:
                print(f'[INFO] {result.stdout.strip()}')
            if result.stderr:
                print(f'[WARN] {result.stderr.strip()}')
            return True
    except FileNotFoundError:
        print('[SKIP] pip-audit not installed. Run: pip install pip-audit')
        return True
    except subprocess.TimeoutExpired:
        print('[WARN] pip-audit timed out')
        return True


def check_file_permissions():
    """Check for common security issues in the project structure.

    Returns:
        bool: True if no critical issues found.
    """
    print('\n' + '=' * 60)
    print('4. PROJECT FILES CHECK')
    print('=' * 60)

    all_ok = True

    # Check .gitignore exists and contains important patterns
    gitignore_path = os.path.join(os.getcwd(), '.gitignore')
    if os.path.exists(gitignore_path):
        required_patterns = ['.env', 'instance/', '*.db', '*.log']
        with open(gitignore_path) as f:
            content = f.read()

        for pattern in required_patterns:
            if pattern in content:
                print(f'[OK] .gitignore contains: {pattern}')
            else:
                print(f'[WARN] .gitignore missing: {pattern}')
                all_ok = False
    else:
        print('[FAIL] .gitignore file not found!')
        all_ok = False

    # Check for .env in working directory (should NOT be committed)
    env_path = os.path.join(os.getcwd(), '.env')
    if os.path.exists(env_path):
        print('[INFO] .env file exists (ensure it is NOT committed)')
    else:
        print('[WARN] No .env file found')

    # Check for leftover .pyc or __pycache__
    pycache_count = 0
    for _root, dirs, files in os.walk(os.getcwd()):
        if '__pycache__' in dirs:
            pycache_count += 1
        for f in files:
            if f.endswith('.pyc'):
                pycache_count += 1
    if pycache_count == 0:
        print('[OK] No __pycache__ or .pyc files found')
    else:
        print(f'[INFO] Found {pycache_count} cache files/dirs (should be in .gitignore)')

    return all_ok


def check_flask_config():
    """Check Flask application configuration for security.

    Returns:
        bool: True if configuration looks secure.
    """
    print('\n' + '=' * 60)
    print('5. FLASK CONFIGURATION CHECK')
    print('=' * 60)

    all_ok = True

    try:
        # The script lives two levels below the project root; without this the
        # import fails and the whole check was silently skipped.
        root = os.path.dirname(os.path.dirname(os.path.dirname(os.path.abspath(__file__))))
        if root not in sys.path:
            sys.path.insert(0, root)

        from app.app import create_app

        # Inspect configuration only: no schema creation, no Discord bot.
        app = create_app(
            {
                'SQLALCHEMY_DATABASE_URI': os.getenv('DATABASE_URL') or 'sqlite:///:memory:',
                'AUTO_CREATE_TABLES': False,
                'ENABLE_DISCORD_BOT': False,
            }
        )

        # Check session cookie settings
        cookie_checks = [
            ('SESSION_COOKIE_SECURE', True, 'Secure cookies'),
            ('SESSION_COOKIE_HTTPONLY', True, 'HttpOnly cookies'),
            ('PERMANENT_SESSION_LIFETIME', 3600, 'Session timeout'),
        ]

        for config_key, expected, description in cookie_checks:
            value = app.config.get(config_key)
            if config_key == 'PERMANENT_SESSION_LIFETIME':
                if value and value <= 3600:
                    print(f'[OK] {description}: {value}s')
                else:
                    print(f'[WARN] {description}: {value}s (should be <= 1 hour)')
                    all_ok = False
            elif value == expected:
                print(f'[OK] {description}: enabled')
            else:
                print(f'[FAIL] {description}: {value}')
                all_ok = False

        # Check MAX_CONTENT_LENGTH
        max_content = app.config.get('MAX_CONTENT_LENGTH')
        if max_content:
            mb = max_content / (1024 * 1024)
            print(f'[OK] MAX_CONTENT_LENGTH: {mb}MB')
        else:
            print('[WARN] MAX_CONTENT_LENGTH not set (unlimited uploads)')
            all_ok = False

        # Check CSRF
        csrf_enabled = app.config.get('WTF_CSRF_ENABLED')
        if csrf_enabled:
            print('[OK] CSRF protection: enabled')
        else:
            print('[FAIL] CSRF protection: disabled')
            all_ok = False

        # Check if app is in DEBUG mode
        if app.debug:
            print('[FAIL] DEBUG mode is enabled!')
            all_ok = False
        else:
            print('[OK] DEBUG mode: disabled')

    except Exception as e:
        # Returning all_ok (still True) here meant that failing to load the
        # application at all was counted as a passing check — the most
        # important section of the report silently never ran.
        print(f'[FAIL] Cannot check Flask config: {e}')
        return False

    return all_ok


def main():
    """Run all security checks and produce a summary report.

    Returns:
        int: 0 if all checks pass, 1 if any fail.
    """
    import argparse

    parser = argparse.ArgumentParser(description='Security validation scanner')
    parser.add_argument(
        '--url',
        default='http://localhost:5000',
        help='Application URL to check headers (default: http://localhost:5000)',
    )
    parser.add_argument(
        '--skip-http',
        action='store_true',
        help='Skip the live HTTP header check (no server running, e.g. in CI)',
    )
    args = parser.parse_args()

    # Plain ASCII: the box-drawing characters this banner used crashed the
    # script outright on a cp1252 Windows console, which is the platform the
    # project is developed and deployed on.
    print('=' * 60)
    print('TEAM TRYOUTS - SECURITY VALIDATION SCANNER')
    print(f'Time: {datetime.now().strftime("%Y-%m-%d %H:%M:%S")}')
    print('=' * 60)

    checks = [check_environment]
    if args.skip_http:
        print('\n[SKIP] HTTP header check disabled via --skip-http')
    else:
        checks.append(lambda: check_https_headers(args.url))
    checks += [
        check_dependencies,
        check_file_permissions,
        check_flask_config,
    ]

    results = []
    for check in checks:
        results.append(check())

    print('\n' + '=' * 60)
    print('SUMMARY')
    print('=' * 60)

    passed = sum(1 for r in results if r)
    failed = sum(1 for r in results if not r)
    total = len(results)

    print(f'Passed: {passed}/{total}')
    print(f'Failed: {failed}/{total}')

    if failed == 0:
        print('\n[OK] All security checks passed!')
        return 0
    print(f'\n[WARN] {failed} check(s) failed. Review the output above.')
    return 1


if __name__ == '__main__':
    sys.exit(main())