In the design of optical systems, simple straightforward requirements are often complicated by unusual and unique constraints. In this particular case a design mapping a 20° square field of view onto a CCD sensor is complicated by the requirement that the wide field of view must not vignette through a narrow-diameter, finite-length cylindrical aperture. Furthermore, the design must use off-the-shelf optics available from any major vendor. The imaging system is designed to operate in the near IR. The 20° square field of view must pass through a 20.32mm diameter, 40mm long cylindrical tube without vignetting. This constraint prohibits the use of a simple achromat whose back focal length would place the image within the cylindrical tube. Two design approaches are discussed, a Keplerian telescope with a field lens, and a reverse telephoto system. Matlab programs have been written that evaluate the first-order optical principles to arrive at a design solution space. Representative solutions are then evaluated in Zemax using the built-in lens catalog to select appropriate lenses. The results show the advantages and limitations of each particular design approach.