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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

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Use performing-cryptographic-audit-of-application to audit [application code and configuration files] in an authorized test or lab environment and deliver a severity-ranked report of cryptographic weaknesses, locations, and remediations, including dependency, certificate/TLS, key-storage, and rotation findings.

Required inputs

  • [application code and configuration files]

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SKILL.md

name: performing-cryptographic-audit-of-applicationdescription: 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, hardcodomain: cybersecuritysubdomain: cryptographytags: - cryptography- audit- security-review- compliance- vulnerability-assessmentversion: '1.0'author: mahipallicense: Apache-2.0nist_csf: - PR.DS-01- PR.DS-02- PR.DS-10mitre_attack: - T1600- T1573- T1553mitre_f3:   version: '1.1'  tactics:   - reconnaissance  - initial-access  - positioning  techniques:   - id: T1557    name: Adversary-in-the-Middle    tactic: positioning    source: attack  - id: T1555    name: Credentials from Password Stores    tactic: reconnaissance    source: attack  - id: F1006.001    name: 'Account Takeover: Exposed API Key'    tactic: initial-access    source: f3  - id: F1004    name: Access with Stolen Session Cookie    tactic: initial-access    source: 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

CategoryExamplesRisk Level
Weak HashingMD5, SHA-1 for integrity/signaturesHigh
Insecure EncryptionDES, 3DES, RC4, BlowfishHigh
Bad Cipher ModeECB mode for any block cipherHigh
Insufficient Key SizeRSA < 2048, AES-128 for long-termMedium
Hardcoded SecretsKeys/passwords in source codeCritical
Weak KDFLow iteration PBKDF2, plain MD5High
Poor Entropytime-based seeds, predictable IVsHigh
Deprecated ProtocolsSSLv3, TLS 1.0, TLS 1.1High

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%