Simulation, machine learning, and data analysis require a wide range of software which can be dependent upon specific operating systems, such as Microsoft Windows. Running this software interactively on massively parallel supercomputers can present many challenges. Traditional methods of scaling Microsoft Windows applications to run on thousands of processors have typically relied on heavyweight virtual machines that can be inefficient and slow to launch on modern manycore processors. This paper describes a unique approach using the Lincoln Laboratory LLMapReduce technology in combination with the Wine Windows compatibility layer to rapidly and simultaneously launch and run Microsoft Windows applications on thousands of cores on a supercomputer. Specifically, this work demonstrates launching 16,000 Microsoft Windows applications in 5 minutes running on 16,000 processor cores. This capability significantly broadens the range of applications that can be run at large scale on a supercomputer.