The transitions between sitting and standing have a high physical and coordination demand, frequently causing falls in older individuals. Rollators, or four-wheeled walkers, are often prescribed to reduce lower-limb load and to improve balance but have been found a fall risk. This study investigated how rollator support affects sit-to-stand and stand-to-sit movements. Twenty young participants stood up and sat down under three handle support conditions (unassisted, light touch, and full support). As increasing task demands may affect coordination, a challenging floor condition (balance pads) was included. Full-body kinematics and ground reaction forces were recorded, reduced in dimensionality by principal component analyses, and clustered by k-means into movement strategies. Rollator support caused the participants to switch strategies, especially when their balance was challenged, but did not lead to support-specific strategies, i.e., clusters that only comprise light touch or full support trials. Three strategies for sit-to-stand were found: forward leaning, hybrid, and vertical rise; two in the challenging condition (exaggerated forward and forward leaning). For stand-to-sit, three strategies were found: backward lowering, hybrid, and vertical lowering; two in the challenging condition (exaggerated forward and forward leaning). Hence, young individuals adjust their strategy selection to different conditions. Future studies may apply this methodology to older individuals to recommend safe strategies and ultimately reduce falls.