Freeform optics have been the subject of much research in recent years. Advances in theories of aberration control, single-point and patch-contact manufacturing methods, and numerical simulation methods make the production of freeform optics realistic for many engineering groups. The feasibility of producing these optical systems introduces new challenges, including dimensional surface metrology, thermo-structural simulations and compensation, and surface finishing methods. As academics and professionals attempt to produce these challenging freeform systems, methods of advancing real-world systems remain relatively scarce.The results of this dissertation are reported through three articles. The first explores production challenges associated with testing a 250 mm diameter telescope, including an example of a significant manufacturing error introduced during the design of the optomechanics. The first article further explores methods for evaluating the telescope’s image quality and the results of applying these tests to the reflective triplet. The second article examines stray light in the same telescope and explores trade-offs between selecting compact mirror arrangements and the presence of unwanted stray light in the freeform telescope. This article presents the design of a basic stray light shroud for the telescope, followed by a simulation of the telescope’s point source transmittance to highlight certain pitfalls of the reflective triplet configuration. The third article builds on the design generated in the second article and explores new techniques to suppress stray light, such as baffling vanes and surface treatments. This article reports the results of surface scatter measurements for materials relevant to the simulation of stray light and gives guidance on methods that other optical engineers may benefit from in their own shroud design process.