This study investigated factors influencing college students' self-directed learning with technology. A questionnaire was employed to obtain data from 153 college students on their self-directed learning readiness, the use of Web 2.0 tools for learning, online communication self-efficacy, and computer self-efficacy to predict their self-directed learning with technology. The data were analysed using sequential multiple regression and mediation analyses. The results showed that the predictor variables explained 19% of the variation in self-directed learning with technology. Self-directed learning readiness and the use of Web 2.0 tools for learning were found to be significant predictors of students' self-directed learning with technology. Moreover, the results indicate that the use of Web 2.0 tools for learning significantly mediated the influence of students' online communication self-efficacy and computer self-efficacy on their self-directed learning with technology. This study suggests that students be provided with scaffolding or assistance, not only for self-directed learning skills and the use of Web 2.0 tools for learning, but also for computer use and online communication in order to enhance their self-directed learning with technology.