Digital video technologies offer a variety of functions for supporting collaborative learning in classrooms. Yet, for novice learners, such as school students, positive learning outcomes also depend centrally on effective social interactions. We present empirical evidence for the positive effects of instructive guidance on performance and on learning of students who use web-based video tools during a short collaborative-design task in their history lesson. In an experiment with 16-year old learners (N = 148) working on a history topic, we compared two contrasting types of guidance for student teams’ collaboration processes (social-interaction-related vs. cognitive-task-related guidance). We also compared two types of advanced video tools. Both types of guidance and tools were aimed at supporting students’ active, meaningful learning and critical analysis of a historical newsreel. Results indicated that social-interaction-related guidance was more effective in terms of learning outcomes (e.g., the students’ history skills) than cognitive-task-related guidance. The different tools did not yield consistent results. The implications of these findings are discussed.