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r509 is a Ruby gem built using OpenSSL that simplifies management of a public key infrastructure. The r509 API helps with CSR creation, signing/parsing of certificates, revocation (CRL/OCSP), and much more. Along with projects like r509-ocsp-responder & r509-ca-http it is a (RFC 5280) certificate authority suitable for production environments.
High Quality Video SIP/IMS client for Google Android
CFSSL: CloudFlare's PKI and TLS toolkit
This Let's Encrypt repo is an ACME client that can obtain certs and extensibly update server configurations (currently supports Apache on .deb based systems, nginx support coming soon)