The license-importance-divide seems almost generational: the aging early adopters still obsess about licenses and younger developers consider licenses more impediments than tools. Yet, the historical focus on licensing in Open Source and Free Software, while occasionally prone to pedantry to a degree only developers can love, stemmed from serious governance considerations for community interaction. Most importantly, a license choice of the project bears more heavily than any other decision on the inherent power dynamics that occur within a FLOSS community.

The licensing infrastructure today also has increased in complexity. Examples of such complexity include: proprietary relicensing business models (which are ostensibly copyleft but push users to buy proprietary licenses), excessive use of CLAs, and tricky clauses on top of existing licenses. The average new contributor rarely has the background knowledge readily available to analyze the community impact on these complex systems.

This talk explores both the historical motivations and modern reactions to licensing matters, and digs deep into understanding how the plethora of policy decisions around licensing, including not just the main license choice, but also CLAs, CAAs, promise documents, and even license bullying tactics, have impacted Open Source and Free Software communities for both good and ill. Attendees can hope to learn some skills for making assessments of licensing regimes in new projects, and the talk serves as a crash-course in quick assessment skills for Open Source community health through the metric of licensing policy.