This research applied Bandura's (1986) social cognitive theory to examine engagement with courseware in traditional and online remedial mathematics learning environments. The study investigated the relationship of courseware engagement to age, computer self-efficacy, computer playfulness, and self-efficacy for self-regulated mathematics learning. The study also analyzed mathematics achievement in terms of engagement, age, gender, mathematics grade self-efficacy, and self-efficacy for self regulated mathematics learning. Participants were 88 students in a traditional environment and 76 students in an online environment. The two groups differed significantly in age, mathematics grade self-efficacy, computer self-efficacy, computer playfulness, courseware engagement, and mathematics achievement. When controlled for age, all significant differences found between the two groups persisted. When controlled for mathematics self-efficacy, the groups no longer differed significantly in mathematics achievement, but all other significant differences remained. Computer self-efficacy and computer playfulness each had a significant association with courseware engagement in the online environment, but not in the traditional environment. Regression models revealed that course setting, age, and self-efficacy for self-regulation jointly predicted engagement with courseware. Both mathematics grade self-efficacy and age jointly predicted achievement. These findings support the views that mathematics self-efficacy is among the most significant predictors of mathematics achievement; computer self-efficacy and computer playfulness are associated with courseware engagement; and self-regulation is an important component of e-learning. Implications for researchers and educators are discussed.