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Seeking to introduce first-year students to library resources and services in an engaging way, an orientation titled The Amazing Library Race (ALR) was developed and implemented at a university library. Informed by the pedagogy of problem-based learning, the ALR asks students to complete challenges regarding different departments and services. This study assesses this initiative’s success using observational and artifact-based data, addressing the challenging prospect of evaluating the impact of library orientation sessions. Two rubrics were developed to measure student involvement and student learning comprehension. More than 14 hours of in-class observations were used to track engagement, and 64 artifacts of student learning were collected and coded to evaluate learning comprehension. After coding, interrater reliability was established using the intraclass correlation coefficient to establish the validity of the ratings. This paper will outline these methodologies, present the results of the data analysis, and discuss the possibilities and difficulties of measuring student engagement in information literacy instruction centred upon active learning.