Researchers have lauded games for their ability to promote situated activity, problem solving, and collaboration. Unfortunately, the characteristics of games vary widely (e.g., content, graphics, technological affordances). Some games constrain player´s experience to a left to right narrative experience (e.g., Mario Brothers) while others immerse the user in a 3D environment with thousands of peers (e.g., EverQuest). Each game is developed using different paradigms, tools, and underlying models; each provides distinct opportunities for learning. However, decades of research has documented that learning benefits are best achieved when we design technology to be closely integrated with objectives for learning and student and teacher interactions. It follows that effective assessment practices must take pedagogical objectives, environment characteristics, and learning affordances into account. As a result, this chapter examines three separate games, educational activities associated with those games, and the distinct assessment approaches involved. Informed by a learning sciences framework and Schrader´s (AACE J 16(4):457-475, 2008) model of technology and learning, we examine assessment of knowledge and skill acquisition as a result of learning from game content in BrainAge ², performance assessment and learning with SPORE, and direct observation assessment strategies when exploring the cognitive and behavioral interactions situated in the World of Warcraft. In each example, we outline the salient properties of these games, the pedagogical implications for learning, and the assessment philosophies and practices they imply.