In the headlong rush to adopt principles like game-based learning and gamification for classroom use, what often happens is that the elements of play, challenge and interactivity so central to successful games are lost, resulting in unengaging “learning app” in the spirit of the “educational CD’s” for which edutainment is remembered today. This is an existential danger for the current cycle of learning games, given that non-existent core gameplay and a diluted focus on learning content were also what made late-era edutainment games neither educational nor particularly entertaining. Indeed, the state of learning games today closely parallels the age of edutainment, which focused on leveraging both new technologies (like personal computer & CDs) and collaborations between educators and developers to create new, more engaging ways of disseminating content. In the 1980s, this convergence of learning, technology, and play resulted in iconic franchises like Oregon Trail and Where in the World is Carmen Sandiego? whose balance of challenge and interactive learning lent them a status beyond being merely entertainment - or merely educational. This spirit of collaboration and discovery also inspired franchises such as SimCity and Age of Empires in the traditional games industry, both of which were well-regarded for their educational content, and were highly successful on the commercial market.In today’s world, for all our literature on best practices and focus on curricula, standards, and connected learning methodologies, as well as a much larger game-playing audience, no app has managed to replicate the success of these decades-old games. In fact, it is likely that today’s entertainment-focused games have done more for education than any current educational title! This panel, primarily aimed at educators and developers, aims to correct this by looking into the commonalities behind the age of edutainment and today’s learning games ecosystem, examining both the critical mistakes being repeated today, as well as how the delicate balance of educational content and engaging gameplay early edutainment espoused not only made early games successful, but has implications for the future development of learning games in the 21st century. Intended Structure: This session is envisioned as a concurrent session (panel), with the 45 minutes structured accordingly. 5 minutes: Panelist Intros 5 minutes: Relevant Background of “edutainment” 25 minute game demos / interactive discussion 10 minutes Q&A Outcomes: Attendees will learn how the state of learning games today closely parallels the early age of edutainment, as well as how many of edutainment’s mistakes are being intentionally - or unintentionally - repeated in the modern era. Attendees will also be given core examples of what went into developing some of the most successful edutainment games, and what practices and lessons they can implement in their own work, with a particular focus on designing for hardware constraints, addressing short attention spans, and how to balance core gameplay with education in and out of the classroom, drawing on re-emergent thinking from an era that fostered interactivity, engagement, and long-term learning.