Difficulties with planning, such as negotiating task understandings and goals, can have a profound effect on regulation and task performance when students work collaboratively (Miller and Hadwin, "Computers in Human Behaviour", 52, 573-588, 2015a). Despite planning being a common challenge, teams often fail to identify strategies for addressing those challenges successfully. The purpose of this study was to examine the effect of team planning support in the form of awareness visualizations (quantified, nominal, and no visualization of individual planning perceptions summarized across group members) on the challenges students face during collaboration, and the ways they report regulating in the face of those challenges. Findings revealed differences across conditions. Individuals in the no visualization condition (a) rated planning as more problematic, and (b) were likely to encounter "doing the task, checking progress", and "group work" challenges when they encounter "planning challenges", (c) reported more "time" and "planning" main challenges compared to "doing the task" and "group work" challenges, and (d) reported that "planning" strategies (adopted as a team) were most effective for addressing planning challenges, followed by "teamwork" strategies which were less effective. In contrast, individuals belonging to groups who received one of the two visualizations (a) reported that both "planning" and "teamwork" strategies to be equally effective for addressing planning challenges, and (b) reported higher levels of success with their strategies than groups without a visualization support. Findings attest to the importance of supporting group planning with planning visualizations.