Community colleges provide educational, social and professional lifelines for students. Community college students are often characterized by their need to balance school amidst conflicting life needs, such as employment and family. As a result, many community college students struggle to find time to commit to on campus classes. Asynchronous online courses offer these students flexibility. Without the ability to self-regulate their learning, this mode of learning has been shown to be more challenging, resulting in students who succeed and persist in coursework less consistently. This quantitative, quasi experimental study involving 92 asynchronous online community college participants from the southeast, explores support structures designed to assist learners in developing effective self-regulation practice. The research combines a two-factor quasi experimental design comparing the use of training that incorporates cognitive modeling, self-reflective prompts and the combination of these elements to evaluate their effect on calibration ability and academic performance. Metacognitive awareness is used as a covariate. Results of this study showed no significant difference between treatment groups in regard to either calibration ability or academic performance based on the elements of the training intervention. Descriptive statistics combine with these results to both support and challenge existing research, and continued research and updates to heuristic practice are suggested. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]