Anthropic-Cybersecurity-Skills/skills/performing-cryptographic-audit-of-application/references/api-reference.md

API Reference: Application Cryptographic Audit

Libraries Used

Library	Purpose
ssl	TLS connection inspection and cipher suite enumeration
socket	TCP connections for TLS handshake testing
cryptography	Certificate parsing, key strength analysis
json	Structure audit findings
datetime	Check certificate validity periods

Installation

pip install cryptography

TLS Configuration Audit

Check TLS Version and Cipher Suite

import ssl
import socket

def check_tls_config(hostname, port=443):
    context = ssl.create_default_context()
    with socket.create_connection((hostname, port), timeout=10) as sock:
        with context.wrap_socket(sock, server_hostname=hostname) as ssock:
            return {
                "hostname": hostname,
                "protocol": ssock.version(),
                "cipher": ssock.cipher()[0],
                "cipher_bits": ssock.cipher()[2],
                "compression": ssock.compression(),
            }

Test for Weak TLS Versions

WEAK_PROTOCOLS = {
    ssl.PROTOCOL_TLSv1: "TLSv1.0",
    ssl.PROTOCOL_TLSv1_1: "TLSv1.1",
}

def test_weak_tls(hostname, port=443):
    findings = []
    for protocol_const, name in WEAK_PROTOCOLS.items():
        try:
            ctx = ssl.SSLContext(protocol_const)
            ctx.check_hostname = False
            ctx.verify_mode = ssl.CERT_NONE
            with socket.create_connection((hostname, port), timeout=5) as sock:
                with ctx.wrap_socket(sock) as ssock:
                    findings.append({
                        "protocol": name,
                        "supported": True,
                        "severity": "high",
                        "issue": f"{name} is supported — deprecated and insecure",
                    })
        except (ssl.SSLError, ConnectionRefusedError, OSError):
            findings.append({"protocol": name, "supported": False})
    return findings

Enumerate Supported Cipher Suites

WEAK_CIPHERS = {
    "RC4", "DES", "3DES", "MD5", "NULL", "EXPORT", "anon", "CBC",
}

def check_cipher_suites(hostname, port=443):
    context = ssl.create_default_context()
    context.set_ciphers("ALL:COMPLEMENTOFALL")
    findings = []
    try:
        with socket.create_connection((hostname, port), timeout=10) as sock:
            with context.wrap_socket(sock, server_hostname=hostname) as ssock:
                cipher_name, protocol, bits = ssock.cipher()
                is_weak = any(w in cipher_name for w in WEAK_CIPHERS)
                findings.append({
                    "cipher": cipher_name,
                    "bits": bits,
                    "weak": is_weak,
                    "severity": "high" if is_weak else "pass",
                })
    except ssl.SSLError as e:
        findings.append({"error": str(e)})
    return findings

Certificate Analysis

Parse and Audit Certificate

from cryptography import x509
from cryptography.hazmat.primitives.asymmetric import rsa, ec
from datetime import datetime, timezone

def audit_certificate(hostname, port=443):
    context = ssl.create_default_context()
    with socket.create_connection((hostname, port), timeout=10) as sock:
        with context.wrap_socket(sock, server_hostname=hostname) as ssock:
            der_cert = ssock.getpeercert(binary_form=True)

    cert = x509.load_der_x509_certificate(der_cert)
    pub_key = cert.public_key()

    findings = []
    # Key strength check
    if isinstance(pub_key, rsa.RSAPublicKey):
        key_size = pub_key.key_size
        if key_size < 2048:
            findings.append({
                "check": "key_size",
                "severity": "critical",
                "detail": f"RSA key {key_size} bits — minimum 2048 required",
            })
    elif isinstance(pub_key, ec.EllipticCurvePublicKey):
        key_size = pub_key.curve.key_size
        if key_size < 256:
            findings.append({
                "check": "key_size",
                "severity": "high",
                "detail": f"EC key {key_size} bits — minimum 256 required",
            })

    # Signature algorithm
    sig_algo = cert.signature_algorithm_oid._name
    if "sha1" in sig_algo.lower():
        findings.append({
            "check": "signature_algorithm",
            "severity": "high",
            "detail": f"SHA-1 signature ({sig_algo}) — deprecated",
        })

    # Validity period
    now = datetime.now(timezone.utc)
    days_remaining = (cert.not_valid_after_utc - now).days
    if days_remaining < 0:
        findings.append({"check": "expiry", "severity": "critical", "detail": "Certificate expired"})
    elif days_remaining < 30:
        findings.append({"check": "expiry", "severity": "warning", "detail": f"Expires in {days_remaining} days"})

    return {
        "subject": cert.subject.rfc4514_string(),
        "issuer": cert.issuer.rfc4514_string(),
        "not_before": cert.not_valid_before_utc.isoformat(),
        "not_after": cert.not_valid_after_utc.isoformat(),
        "days_remaining": days_remaining,
        "serial_number": hex(cert.serial_number),
        "signature_algorithm": sig_algo,
        "key_type": "RSA" if isinstance(pub_key, rsa.RSAPublicKey) else "EC",
        "key_size": key_size,
        "findings": findings,
    }

Check HSTS Header

import requests

def check_hsts(url):
    resp = requests.get(url, timeout=10, allow_redirects=True)
    hsts = resp.headers.get("Strict-Transport-Security", "")
    findings = []
    if not hsts:
        findings.append({"check": "hsts", "severity": "medium", "detail": "HSTS header missing"})
    else:
        if "includeSubDomains" not in hsts:
            findings.append({"check": "hsts", "severity": "low", "detail": "HSTS missing includeSubDomains"})
        max_age = 0
        for part in hsts.split(";"):
            if "max-age" in part:
                max_age = int(part.split("=")[1].strip())
        if max_age < 31536000:
            findings.append({"check": "hsts_max_age", "severity": "low", "detail": f"max-age {max_age} < 1 year"})

    return {"hsts_header": hsts, "findings": findings}

Output Format

{
  "hostname": "example.com",
  "tls_version": "TLSv1.3",
  "cipher": "TLS_AES_256_GCM_SHA384",
  "certificate": {
    "subject": "CN=example.com",
    "issuer": "CN=R3,O=Let's Encrypt",
    "days_remaining": 62,
    "key_type": "EC",
    "key_size": 256
  },
  "weak_tls_supported": ["TLSv1.0"],
  "hsts_enabled": true,
  "findings": [
    {
      "check": "weak_tls",
      "severity": "high",
      "detail": "TLSv1.0 is supported — deprecated and insecure"
    }
  ]
}