According to Pearson’s Law: “That which is measured improves.” But some important constructs, like problem-solving skill, are generally viewed as very difficult to measure for a variety of reasons (e.g., lack of a clear and agreed-upon definition, psychological and/or statistical multidimensionality of the construct, subjectivity of scoring, and so on). Adding to the challenge of validly measuring problem-solving skill is that formal education settings tend to focus only on well-structured problems – those that have correct and incorrect answers. However, these problems tend to have little transfer to the real world. In short, there is a gap in the kinds of problems being assessed and taught in schools and those desired in workplace environments. In this chapter, we focus on how game-based immersive environments, such as well-designed video games, can be used to both measure and promote the development of problem-solving skills in formal education settings. In this chapter, we discuss the theoretical foundations of problem-solving and provide a worked example of assessing it from gameplay using a well-designed video game. We conclude the chapter with a discussion on future implications for using game-based environments to measure and promote problem-solving skills in education.