High speed rotorcraft transmissions are subject to load-independent power losses consisting of drag loss and pumping loss. Tightly conforming shrouds enclosing the transmission gears are often incorporated to reduce the drag component of the total load-independent losses. However, tightly conforming axial shrouds can result in an increase in the pumping loss component. Quantifying the pumping loss of shrouded gear transmissions has been the subject of many studies. This study presents a new approach for estimating pumping loss based on the concept of swept volume and examines the applicability of the approach to various shroud configurations. The drag loss and pumping loss of a shrouded spur gear pair have been determined through testing using the NASA Glenn Research Center (GRC) Gear Windage Test Facility. The results from this testing have been compared to theoretical results using the formulations presented in this study. In addition, computational fluid dynamics (CFD) analysis has been conducted for the various shroud configurations tested at NASA GRC. The results from the CFD analysis confirm the theoretical and empirical results and provide insight into the applicability of the swept volume approach for estimating pumping power loss of shrouded gear transmissions.