This chapter describes how the situative theories of engagement and motivation explored in Hickey and Granade (2004) have evolved in subsequent refinements of a comprehensive approach to online instruction and assessment. Situative theories were used to design and refine courses for secondary, undergraduate, graduate, and open learners, mostly using typical features of common learning management systems. This work has resulted in generalizable design principles for motivating productive forms of disciplinary engagement in online settings. The chapter first highlights broader relevant developments since 2004, provides some historical context regarding situative approaches to motivation, and summarizes an empirical test of situated motivation. The chapter then describes how the core set of educational design principles emerged across cycles of design-based research across several educational technologies, including online courses. The chapter then uses examples from a graduate-level Learning Sciences course to illustrate the current design principles and describe how they support engagement and achievement, while accommodating diversity in prior experience, current application context, and future goals.