Online programs are growing exponentially; the structure, program design, and instructional strategies used determine learner success and the viability of online programs. Instructors are expected to demonstrate competence as online facilitators, creating an educational experience that meets the demands of 21st-century teaching and learning. In turn, learners are expected to demonstrate readiness for learning. The community of inquiry (CoI) model was used as the framework to understand the phenomenon of establishing teaching presence and the implications in improving learner success. There is a paradigm shift in teaching and learning online, and many universities and colleges see this as an opportunity to create niche markets and augment new horizons. However, learners may not naturally have the proclivity to manage and direct their learning, and stimuli for learning are not always packaged to guarantee learner success. For this research, understanding how teaching presence is established in higher education classrooms in the Jamaican context was explored. The CoI model was instrumental in measuring learners' engagement in both synchronous and asynchronous environments. The exploration identified trends, characteristics, patterns, and behaviors of online instructors establishing teaching presence in higher education classrooms in Jamaica. The research investigated how online instructors establish teaching presence in synchronous or asynchronous courses, exploring the fundamental principles that they use to keep students motivated and engaged online. The probability that learners are successful hinges on the climate created by instructors and the quality of the course design, thus increasing the overall mandate of how instructors establish teaching presence. [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.]