First Software Freedom Day CTF: reflections

Software Freedom Day, a yearly shindig dedicated to free and open-source software (FOSS), is a time to champion its use and educate the masses. Things were spiced up this year with a Capture the Flag (CTF) event on the CTF'd platform! Think of it as a digital treasure hunt where participants, armed with their cybersecurity skills, solve challenges to find hidden "flags." Popular platforms like "Try Hack Me" host CTFs, but we decided to craft our own, inspired by the Freedom Ladder - a guide to increasing your software freedom. We had to skip a few steps due to time constraints (blame it on the coffee breaks).

Our challenges ranged from deciphering Richard Stallman's musings in a .docx file (metadata, anyone?) to cracking GnuPG-encrypted files (cue dramatic music). We even hid a flag in the support chat (Revolt.chat or IRC - old school cool) and on Distrowatch.com's advanced search page (for the truly adventurous).

The echoing silence that followed my impassioned call for Software Freedom Day Capture the Flag participants was a stark contrast to the vibrant enthusiasm I had envisioned. I had naively assumed the Cyber Resilience community was teeming with GNU/Linux devotees, eager to showcase their skills in a contest celebrating open-source software. The reality was far less inspiring.

Weeks melted into days, and the number of registered "nerds" remained disappointingly low. My initial optimism curdled into a nagging self-doubt. Had I misjudged the community's interests? Was my contest simply not appealing enough? The lack of participation from the broader community gnawed at me, forcing me to confront the possibility that the problem lay not with them, but with me.

Perhaps my outreach efforts were lackluster, failing to ignite the spark of excitement I felt so keenly. Maybe my assumptions about the community's demographics were off-base. Whatever the reason, the responsibility for the underwhelming response rested squarely on my shoulders.

This experience served as a humbling reminder that even the most well-intentioned endeavors can fall flat without effective planning and execution. It taught me the importance of thorough research, clear communication, and a willingness to adapt to unforeseen challenges. While the outcome wasn't what I had hoped for, it was a valuable lesson in the complexities of community engagement and the importance of self-reflection in the face of adversity.

We hoped for a bustling crowd, but alas, only a few brave souls ventured forth. And while no one conquered all the challenges (phew, my wallet is safe!), we applaud their efforts. Kudos to the Digital Freedom Foundation for championing this global event and to CTF'd for their generous discount on their open-source platform. Big shoutouts also go to LibrePlanet, the Free Software Foundation, Canonical, Ubuntu, Distrowatch.com, Black Hills Information Security, the Peoria Area Amateur Radio club, and Three Sisters Park in Chillicothe, Illinois. You guys rock!

So, until next year's Software Freedom Day (mark your calendars for the third Saturday of September), let's keep celebrating the freedom to tinker, share, and improve software. Remember, free software isn't just about cost; it's about liberty!