Pupil imaging performance is analyzed from the perspective of physical optics. A multi-plane diffraction model is constructed by propagating the scalar electromagnetic field, surface by surface, along the optical path comprising the pupil imaging optical system. Modeling results are compared with pupil images collected in the laboratory. The experimental setup, although generic for pupil imaging systems in general, has application to the James Webb Space Telescope (JWST) optical system characterization where the pupil images are used as a constraint to the wavefront sensing and control process. Practical design considerations follow from the diffraction modeling which are discussed in the context of the JWST Observatory
