Anthropic-Cybersecurity-Skills/skills/performing-ssl-certificate-lifecycle-management/SKILL.md

name, description, domain, subdomain, tags, version, author, license

name	description	domain	subdomain	tags	version	author	license
performing-ssl-certificate-lifecycle-management	SSL/TLS certificate lifecycle management encompasses the full process of requesting, issuing, deploying, monitoring, renewing, and revoking X.509 certificates. Poor certificate management is a leading	cybersecurity	cryptography	cryptography ssl certificates pki tls key-management	1.0	mahipal	MIT

Performing SSL Certificate Lifecycle Management

Overview

SSL/TLS certificate lifecycle management encompasses the full process of requesting, issuing, deploying, monitoring, renewing, and revoking X.509 certificates. Poor certificate management is a leading cause of outages and security incidents. This skill covers automating the entire certificate lifecycle using Python and ACME protocol tools.

Objectives

• Generate Certificate Signing Requests (CSRs) programmatically
• Parse and validate X.509 certificates
• Monitor certificate expiration across infrastructure
• Automate renewal using ACME protocol (Let's Encrypt)
• Implement certificate revocation checking (CRL and OCSP)
• Track certificate inventory across multiple domains

Key Concepts

Certificate Lifecycle Stages

1. Request: Generate key pair and CSR
2. Issuance: CA validates and issues certificate
3. Deployment: Install certificate on servers
4. Monitoring: Track expiration and health
5. Renewal: Request new certificate before expiry
6. Revocation: Invalidate compromised certificates

Certificate Types

Type	Validation	Use Case
DV (Domain Validation)	Domain ownership	Websites, APIs
OV (Organization Validation)	Domain + org identity	Business sites
EV (Extended Validation)	Full legal verification	E-commerce, banking
Wildcard	*.domain.com	Multi-subdomain
SAN/UCC	Multiple domains	Multi-domain hosting

Security Considerations

• Set up automated monitoring for all certificates
• Use ECDSA (P-256) certificates for better performance over RSA
• Enable OCSP stapling on all servers
• Implement Certificate Transparency log monitoring
• Maintain inventory of all certificates and their locations
• Plan for CA compromise scenarios (key pinning, backup CAs)

Validation Criteria

• CSR generation produces valid PKCS#10 request
• Certificate parsing extracts all relevant fields
• Expiration monitoring detects certificates within threshold
• Certificate chain validation verifies trust path
• OCSP checking detects revoked certificates
• Certificate inventory tracks all deployed certificates