The current study investigates whether students’ tool use in a Content Management Systems (CMSs) for example, blackboard, WebCT, relates to students’ strategy use within a CMS-supported course. In this way, the study strives to explain the tool use differences, and furthermore, it strives to find (online) behavioral indications for students’ strategy use. Data were collected within a first-year undergraduate course “Learning & Instruction”. Students ( n = 182 ) reported their strategy use as measured through the Inventory of Learning Styles (Vermunt, 1998). Students’ tool use within the CMS was logged. K-means cluster analyses revealed four clusters that were characterized by different strategies and accompanying tool use. Specifically, two clusters revealed a tool use pattern that was in line with the behavioral profile of students’-reported strategy use. Interestingly, two clusters revealed a tool use pattern that was in contrast to the reported strategy use. These results raise questions with respect to students’ tool perceptions and students’ calibration capacities.