Game-based assessments and learning environments create unique opportunities to provide learners with the ability to demonstrate their proficiency with cognitive skills and behaviors in increasingly authentic environments. Effective task designs, and the effective alignment of tasks with constructs, are also improving our ability to provide learners with insights about their proficiency with these skills. Sharing these insights within the industry with those working toward the same goal contributes to the rising tide that lifts all boats. In this paper we present insights from our work to develop and measure collaborative problem solving skills using a game-based assessment “Circuit Runner.” Our innovative educational game design allows us to incorporate item response data, telemetry data, and stealth- telemetry data to provide a more authentic measure of collaborative problem solving skills. Our study design included 379 study participants on Amazon Mechanical Turk (MTurk), who completed the “Circuit Runner” CPS assessment. The paper provides details on the design of educational games and scoring techniques and discusses findings from the pilot study.