Work in cognitive and educational psychology examines a variety of phenomena related to the learning and retrieval of information. Indeed, Alice Healy, our honoree, and her colleagues have conducted a large body of groundbreaking research on this topic. In this article we discuss how 3 learning principles (the generation effect, deliberate practice and feedback, and antidotes to disengagement) discussed in Healy, Schneider, and Bourne (2012) have influenced the design of 2 intelligent tutoring systems that attempt to incorporate principles of skill and knowledge acquisition. Specifically, this article describes iSTART-2 and the Writing Pal, which provide students with instruction and practice using comprehension and writing strategies. iSTART-2 provides students with training to use effective comprehension strategies while self-explaining complex text. The Writing Pal provides students with instruction and practice to use basic writing strategies when writing persuasive essays. Underlying these systems are the assumptions that students should be provided with initial instruction that breaks down the tasks into component skills and that deliberate practice should include active generation with meaningful feedback, all while remaining engaging. The implementation of these assumptions is complicated by the ill-defined natures of comprehension and writing and supported by the use of various natural language processing techniques. We argue that there is value in attempting to integrate empirically supported learning principles into educational activities, even when there is imperfect alignment between them. Examples from the design of iSTART-2 and Writing Pal guide this argument.