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Ride-pooling, which accommodates multiple passenger requests in a single trip, has the potential to substantially enhance the throughput of mobility-on-demand (MoD) systems. This paper investigates MoD systems that operate mixed fleets composed of “basic supply” and “augmented supply” vehicles. When the basic supply is insufficient to satisfy demand, augmented supply vehicles can be repositioned to serve rides at a higher operational cost. We formulate the joint vehicle repositioning and ride-pooling assignment problem as a two-stage stochastic integer program, where repositioning augmented supply vehicles precedes the realization of ride requests. Sequential ride-pooling assignments aim to maximize total utility or profit on a shareability graph: a hypergraph representing the matching compatibility between available vehicles and pending requests. Two approximation algorithms for midcapacity and high-capacity vehicles are proposed in this paper; the respective approximation ratios are [Formula: see text] and [Formula: see text], where p is the maximum vehicle capacity plus one. Our study evaluates the performance of these approximation algorithms using an MoD simulator, demonstrating that these algorithms can parallelize computations and achieve solutions with small optimality gaps (typically within 1%). These efficient algorithms pave the way for various multimodal and multiclass MoD applications. History: This paper has been accepted for the Transportation Science Special Issue on Emerging Topics in Transportation Science and Logistics. Funding: This work was supported by the National Science Foundation [Grants CCF-2006778 and FW-HTF-P 2222806], the Ford Motor Company, and the Division of Civil, Mechanical, and Manufacturing Innovation [Grants CMMI-1854684, CMMI-1904575, and CMMI-1940766]. Supplemental Material: The online appendix is available at https://doi.org/10.1287/trsc.2021.0349 .