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We present an automated method of finding different freeform dioptric starting systems, working in the infrared region, for further optimization in commercial optical design software. Our developed method couples the simultaneous multiple surface (SMS) method, introduced by Benítez and Miñano, with automatic optimization in Zemax OpticStudio. The method allows an optical designer to explore the merit function (MF) landscape of freeform optical problems. In this article, we apply our method to a size, weight, and power (SWaP) problem, and we compare our designed system with a system found in the literature that has the same aperture of F/1.2. Then, we increase the aperture of the system up to F/0.9, taking advantage of the use of freeform surfaces.