The purpose of this study was to examine the relationship among students' characteristics, self-regulated learning, technology self-efficacy, and course outcomes in online learning settings. Previous research provided conflicting evidence regarding the relationship among these variables. Further, there is no prior research that has examined these variables simultaneously. In addition, there has been limited research examining self-regulated learning as the mediator between students' characteristics and course outcomes. Therefore, a hypothesized model was generated based on previous empirical studies. Two hundred and fifty-six students participated in this study. All participants completed an online survey hosted via SurveyMonkey.com. The survey consisted of a total of 130 items with a demographic questionnaire, the Modified Motivation Strategies Learning Questionnaire, the Open-ended Learning Strategies Questionnaire, the Online Technology Self-Efficacy Scale, the Course Satisfaction Questionnaire, and the final grades. Structural Equation Modeling was served as the major data analysis method. The results indicated that the initially hypothesized was not an appropriate model in terms of explaining the relationship among students' characteristics, self-regulated learning, technology self-efficacy, and course outcomes. After model re-specification, a final model with good fit was obtained. Based on the results from the final model, the number of previous online courses taken directly influenced the effectiveness of students' learning strategies in taking online courses, and then, directly affected the students' levels of motivation. Students' levels of motivation influenced their levels of technology self-efficacy and course satisfaction. Finally, their levels of technology self-efficacy and course satisfaction affected their final grades. In other words, students with previous online learning experiences tended to have more effective learning strategies when taking online courses, and hence, had higher levels of motivation in their online courses. When students had higher levels of motivation in their online courses, their levels of technology self-efficacy increased, and their levels of course satisfaction also increased. As their levels of technology self-efficacy and course satisfaction increased, their final grade tended to be better than the students who did not have experiences in taking online courses. In order to understand the specific learning strategies students used in taking online courses, four open-ended questions which were modified from Self-Regulated Learning Interview Schedule (Zimmerman & Martinez-Pons, 1986) were used. The results indicated that students used planners/calendars, and reviewing Blackboard and syllabus in order to keep up with the assignments. Most of the students took notes in terms of remembering the learning materials and some reviewed the stream videos. In addition, in order to review the learning materials, students downloaded the files posted on the Blackboard and made hard copies to have everything handed. While taking online courses, students used search engine, Blackboard, and online library a lot in order to obtain more information. They also reported that the e-mails and discussion board were very useful in terms of interacting with the instructors and their classmates. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]