The main objective of the study is to develop an interactive assessment game using Python. Colegio De San Gabriel Arcangel, since its foundation in 1993, has never tried to create a gamified assessment or reviewer to keep their students engaged in learning. Given the background and exposure to computer operations and programming, the proponents developed an interactive assessment game called The Adventures of Tom to quantify the proficiency of students and aid the students in their learning and review. The Adventures of Tom embodied the qualities of a good software package. It is equipped with quests and lesson delivery, program tracker, review questions and assessments that quickly present results after its duration. The subject covered by the study is Computer Programming 1 covering topics on introduction to programming concepts, logic formulation, and introduction the Java programming language and its features. The descriptive method of research was used. Specifically, survey questionnaires were used in the collection of data from the respondents namely the BSCS freshmen students of CDSGA who are currently enrolled in the abovementioned subject. The Slovin formula was used to determine the number of student-respondents. Interview was also conducted for additional data. The information entered into the instrument was drawn from ISO 9126 Standards for Evaluation of Software Quality particularly metrics on Functionality, Reliability, Usability, and Efficiency. The metrics for Portability and Maintainability were not included as these were hard to measure by the respondents.