Student question-generation has been suggested as an engaging and constructive learning strategy. However, little is known about what learners’ perceived value of and difficulty with this strategy are, if and how such variables contribute to cognitive engagement and achievement, and whether and how such variables interact to affect learning. A series of correlational statistics and hierarchical regression analyses done on a group of 50 university students exposed to its extended use in a classroom setting revealed several findings: first, participants generally perceived student question-generation as useful and beneficial for both their current and future learning; second, the introduced task presented itself as an intrinsic motivational learning activity that was optimally challenging; third, participants with more positive value tended to employ more cognitive and metacognitive strategies while learning; fourth, participants who perceived the task in which they were engaged as more difficult tended to perform better on academic assessments, and finally, this study revealed how perceived value interacts with perceived difficulty to affect learning. Interaction effects on both employed cognitive and metacognitive strategies were supported. Implications for instructional implementation, limitations of this study and recommendations for directions for future studies are provided.