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Anthropic-Cybersecurity-Skills/skills/performing-cryptographic-audit-of-application/SKILL.md
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name, description, domain, subdomain, tags, version, author, license, nist_csf, mitre_attack, mitre_f3
name description domain subdomain tags version author license nist_csf mitre_attack mitre_f3
performing-cryptographic-audit-of-application A cryptographic audit systematically reviews an application's use of cryptographic primitives, protocols, and key management to identify vulnerabilities such as weak algorithms, insecure modes, hardco cybersecurity cryptography
cryptography
audit
security-review
compliance
vulnerability-assessment
1.0 mahipal Apache-2.0
PR.DS-01
PR.DS-02
PR.DS-10
T1600
T1573
T1553
version tactics techniques
1.1
reconnaissance
initial-access
positioning
id name tactic source
T1557 Adversary-in-the-Middle positioning attack
id name tactic source
T1555 Credentials from Password Stores reconnaissance attack
id name tactic source
F1006.001 Account Takeover: Exposed API Key initial-access f3
id name tactic source
F1004 Access with Stolen Session Cookie initial-access f3

Performing Cryptographic Audit of Application

Overview

A cryptographic audit systematically reviews an application's use of cryptographic primitives, protocols, and key management to identify vulnerabilities such as weak algorithms, insecure modes, hardcoded keys, insufficient entropy, and protocol misconfigurations. This skill covers building an automated crypto audit tool that scans Python and configuration files for common cryptographic weaknesses.

When to Use

  • When conducting security assessments that involve performing cryptographic audit of application
  • When following incident response procedures for related security events
  • When performing scheduled security testing or auditing activities
  • When validating security controls through hands-on testing

Prerequisites

  • Familiarity with cryptography concepts and tools
  • Access to a test or lab environment for safe execution
  • Python 3.8+ with required dependencies installed
  • Appropriate authorization for any testing activities

Objectives

  • Detect usage of deprecated algorithms (MD5, SHA-1, DES, RC4)
  • Identify insecure cipher modes (ECB) and padding schemes
  • Find hardcoded keys, passwords, and secrets in source code
  • Verify TLS/SSL configuration strength
  • Check key derivation function parameters
  • Validate random number generator usage
  • Produce a structured audit report with findings and remediation

Key Concepts

Cryptographic Weakness Categories

Category Examples Risk Level
Weak Hashing MD5, SHA-1 for integrity/signatures High
Insecure Encryption DES, 3DES, RC4, Blowfish High
Bad Cipher Mode ECB mode for any block cipher High
Insufficient Key Size RSA < 2048, AES-128 for long-term Medium
Hardcoded Secrets Keys/passwords in source code Critical
Weak KDF Low iteration PBKDF2, plain MD5 High
Poor Entropy time-based seeds, predictable IVs High
Deprecated Protocols SSLv3, TLS 1.0, TLS 1.1 High

Security Considerations

  • Review both application code and configuration files
  • Check third-party dependencies for known crypto vulnerabilities
  • Verify certificates and TLS configurations on deployed servers
  • Ensure secrets are loaded from environment variables or vaults
  • Review key storage and rotation practices

Validation Criteria

  • Scanner detects all injected test weaknesses
  • MD5/SHA-1 usage for security purposes is flagged
  • ECB mode usage is flagged
  • Hardcoded keys/passwords are detected
  • Weak KDF parameters are identified
  • Report includes severity, location, and remediation
  • False positive rate is below 10%