In an educational setting, the use of online learning tools impacts student performance. Motivation and beliefs play an important role in predicting student decisions to use these learning tools. However, IT-personality entailing playfulness on the web, perceived personal innovativeness, and enjoyment may have an impact on motivations. In this study, we investigate the influence of IT-personality traits on motivation and beliefs. The study includes 95 participants. A survey was conducted after using the learning tool for one semester. Assessment of the psychometric properties of the scales proved acceptable and confirmatory factor analysis supported the proposed hypotheses. With the exception of the impact of enjoyment on motivation, all other hypotheses demonstrate behavior different from other contexts: playfulness on the web and perceived personal innovativeness have little to no impact on motivation; motivation in turn has the opposite strong and significant effect on beliefs. Specifically, we found that motivation has a strong impact on students’ attitudes and consequently attitudes were found to determine intentions where the variance explained is 50% (attitude) and 28% (intentions). These results give way to interesting interpretations as they relate to learning.