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Given the clear need to better understand planning as a core sub-process within self-regulated learning, we investigated how students plan for their learning and whether their planning differs depending upon the demands of the learning context. A sample of 159 students completed a task in which they read a series of vignettes with different contextual demands. For each vignette, students selected specific learning and motivational strategies, indicated the planned order of use, and allocated time for each strategy. We found that students were generally effective in matching their planning to the contextual demand for learning strategies, but less so for motivational strategies. Moreover, students’ general perceptions of the strategies (effectiveness, frequency, difficulty of use) were significantly associated with effective planning.