This study first examined the factors that enhance learning effectiveness and student satisfaction when an interactive response system (IRS) is introduced to a financial planning course. Second, we examined the influence of the initial experience of using an IRS on subsequent learning results. A total of 217 financial practitioners participated in a three-session financial course. During the course, the instructor interacted with the participants using the IRS. Participants were asked to use the smartphone-based IRS to interact with their instructor, and they were requested to complete two tests (a pretest and a posttest) and a satisfaction survey after each session. Participation data were directly imported into the UMU system for statistical analysis. The results indicated that task-technology fit (TTF) and instructor ability were predictors of learning effectiveness and student satisfaction. The perception of TTF in the first session had a positive effect on the cognitive results in the subsequent stages, which was the primacy effect. Moreover, a recency effect was observed in the affective results, meaning that the influence of the perception of TTF and instructor ability in the concurrent session on student satisfaction was stronger than the influence of previous experiences. Research and practical implications are presented to conclude the paper.