The goal of this dissertation was to document and analyze ways in which a game can be a valid and useful assessment of teachers' competency for the wise integration of technology in the classroom. Using concepts from ecological psychology and situated cognition, this study analyzed card and board games as measures of the situative and interactive aspect of teachers' pedagogical design thinking in relation to technology integration. To achieve this goal, this dissertation project was comprised of three studies, featuring a theoretical framework whitepaper, a design experiment report, and an omnibus research study. Chapter 1 describes teachers' on-the-fly pedagogical reasoning in relation to technology integration and proposes an expanded framework for teacher competency with technology called TPACK-L framework. Chapter 2 proposes an alternative game-based assessment framework called Playful Assessment. Drawing from the proposed framework, Chapter 2 presents a game-based assessment practice as an alternative and useful way to assess the situative and interactive aspect of teachers' cognition and action in relation to technology integration. Lastly, Chapter 3 utilizes a newly developed board game, "EXPERTISE," as an assessment environment and examines to what extent the designed game can serve as a valid and useful assessment tool for assessing teachers' competencies with technology integration into their classrooms. Particularly, Chapter 3 provides empirical evidence showing that gameplay outcomes can be used to estimate teachers' competencies with technology integration in an ecologically valid way. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]