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Cryptography OpenPGP OpenSSL Digital ID Dev Tools Digital Security

Cryptography

art and science of securing information by converting it into an unreadable format for unauthorized users

Cryptographic Tools for securing/signing files/documents/commits

  • email, file, git signatures
    • OpenPGP: GnuPG (GPG) with GUIs -- Kleopatra (Windows), GPG Suite (macOS), Seahorse (Linux), Gpg4win
  • X.509 certificates / test signing
    • OpenSSL: create self-signed certs, create .pfx/.p12
  • real trusted TLS certificates (websites)
    • Let’s Encrypt + Certbot (free, automated CA)
  • sign code / git commits
    • GPG (git commit -S)
    • SSH commit signing (Git >=2.34)
    • GitHub accepts GPG/SSH public keys
  • key/passphrase/encrypted backups storage & passphrase management
    • Bitwarden (free tier), KeePass (free, local)
    • OS keystores: Windows Certificate Store, macOS Keychain, Linux secret stores
  • backup and offline storage
    • encrypted containers: VeraCrypt
    • encrypted PFX files made with OpenSSL
  • device-backed keys:
    • use your platform authenticator (WebAuthn) — built-in and free;
    • hardware tokens cost money (not free)
  • host public GPG keys for commit verification; accept signed commits/tags
    • Github
  • passwordless logins
    • Platform authenticators
    • WebAuthn (built into browsers & OS)
  • Key servers for distributing public OpenPGP keys
    • hkp
    • SKS pools; use modern keyservers or upload to GitHub instead

OpenSSL vs `LibreSSL:

  • OpenSSL: already available on Ubuntu Linux distribution
  • LibreSSL: already available on macOS
Feature OpenSSL LibreSSL
Origin Established in 1998 Forked from OpenSSL in 2014 by OpenBSD
Development Philosophy Extensive feature set and broad compatibility Focus on code quality, security, and simplicity
Maintenance Maintained by the OpenSSL Project Maintained by the OpenBSD Project
Codebase Quality Larger and more complex codebase Cleaner codebase with many legacy parts removed
Security Focus Regular updates and broad support Strong emphasis on security best practices
Compatibility Broad compatibility with many systems and applications May lack some legacy features; focused on modern security practices
Use Cases Widely used in web servers, embedded systems, and applications Used in security-focused environments like OpenBSD
Documentation and Support Extensive documentation and community support Strong community support, especially within OpenBSD
OS Support Cross-platform, supports most major operating systems including Windows, Linux, macOS, and Unix variants Primarily developed for OpenBSD; also supports other Unix-like systems including Linux and macOS