In the early 2000s, the Apache HTTP Server dominated the web, powering most websites with its open-source flexibility. However, in 2004, the release of the Apache License 2.0 introduced controversial clauses—particularly around patent grants and indemnification—that raised serious concerns within the security-focused OpenBSD project. OpenBSD, known for its rigorous code auditing and ’secure by default’ philosophy, viewed these legal terms as unacceptable risks that could compromise user freedom and expose users to unforeseen liabilities. Rather than adopt the new license, the OpenBSD team, led by Theo de Raadt, made a bold decision: they forked the last Apache 1.3 version under the trusted license and began building their own minimalist, security-hardened web server from the ground up—OpenBSD Httpd. This wasn’t a move driven by performance or feature competition, but by an unwavering commitment to transparency, legal clarity, and user trust. The resulting Httpd incorporated advanced security mechanisms like privilege separation—where different server processes run with minimal permissions—and chrooting, which confines the server to a restricted file system to limit damage from potential breaches. Over time, Httpd evolved to support essential features like TLS encryption and FastCGI, but always in line with OpenBSD’s core principles of simplicity and auditability. While it never aimed to rival giants like Apache or Nginx in scale, OpenBSD Httpd became a critical tool for environments where security is paramount: small businesses, privacy-conscious organizations, educational institutions, and developers who prioritize integrity over convenience. Its influence extends beyond its user base, serving as a model for secure software design and reinforcing the idea that digital trust must be built on both technical excellence and ethical rigor. The story of OpenBSD Httpd underscores a pivotal truth in technology: behind every secure connection lies not just code, but choices—choices rooted in philosophy, principle, and the quiet courage to walk away from the mainstream when core values are at stake. As cybersecurity threats grow more sophisticated, the legacy of this principled fork continues to inspire a deeper understanding of what it means for software to be truly free, safe, and trustworthy.