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Online learning readiness is fundamental to student successful participation, presence, and interaction in online courses. Effective facilitation of these key components depends on sound instructional design. In self-directed online environments, learner-content interaction and scaffolding self-regulated learning have been found of primary importance to generate meaningful learning. To provide a solution to the challenges of interoperability of various functions in synchronous online learning environments, this chapter presents a case study about the design and development of a self-paced orientation to help students acquire online learning readiness. Learner-content interaction is strategically utilized in the design to scaffold self-regulated learning. The results of the case study demonstrate that this orientation positively prepares students to be ready for learning in a synchronous online environment. The approach can be of practical use to individuals and groups.