Anthropic-Cybersecurity-Skills configuring-certificate-authority-with-openssl

A Certificate Authority (CA) is the trust anchor in a PKI hierarchy, responsible for issuing, signing, and revoking

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T=$(mktemp -d) && git clone --depth=1 https://github.com/mukul975/Anthropic-Cybersecurity-Skills "$T" && mkdir -p ~/.claude/skills && cp -r "$T/skills/configuring-certificate-authority-with-openssl" ~/.claude/skills/mukul975-anthropic-cybersecurity-skills-configuring-certificate-authority-with-o && rm -rf "$T"
manifest: skills/configuring-certificate-authority-with-openssl/SKILL.md
source content

Configuring Certificate Authority with OpenSSL

Overview

A Certificate Authority (CA) is the trust anchor in a PKI hierarchy, responsible for issuing, signing, and revoking digital certificates. This skill covers building a two-tier CA hierarchy (Root CA + Intermediate CA) using OpenSSL and the Python cryptography library, including CRL distribution, OCSP responder configuration, and certificate policy management.

When to Use

  • When deploying or configuring configuring certificate authority with openssl capabilities in your environment
  • When establishing security controls aligned to compliance requirements
  • When building or improving security architecture for this domain
  • When conducting security assessments that require this implementation

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

  • Create a Root CA with self-signed certificate
  • Create an Intermediate CA signed by the Root CA
  • Issue server and client certificates from the Intermediate CA
  • Configure Certificate Revocation Lists (CRLs)
  • Implement certificate policies and constraints
  • Build a complete PKI hierarchy programmatically

Key Concepts

CA Hierarchy

Root CA (offline, air-gapped)
  |
  +-- Intermediate CA (online, operational)
        |
        +-- Server Certificates
        +-- Client Certificates
        +-- Code Signing Certificates

Certificate Extensions

ExtensionPurposeCritical
basicConstraintsCA:TRUE/FALSE, pathLenConstraintYes
keyUsagekeyCertSign, cRLSign, digitalSignatureYes
extendedKeyUsageserverAuth, clientAuth, codeSigningNo
subjectKeyIdentifierHash of public keyNo
authorityKeyIdentifierIssuer's key identifierNo
crlDistributionPointsURL to CRLNo
authorityInfoAccessOCSP responder URLNo

Security Considerations

  • Root CA private key must be stored offline (air-gapped HSM)
  • Use minimum 4096-bit RSA or P-384 ECDSA for CA keys
  • Set path length constraints on intermediate CAs
  • Implement certificate policies (OIDs)
  • Enable CRL and OCSP for revocation checking
  • Audit all certificate issuance operations

Validation Criteria

  • Root CA self-signed certificate is valid
  • Intermediate CA certificate chains to Root CA
  • Issued certificates chain to Intermediate -> Root
  • Path length constraints are enforced
  • CRL is generated and accessible
  • Revoked certificates appear in CRL
  • Certificate policies are correctly embedded