We investigate the feasibility of discriminating between single-layered clouds and multi-layered clouds where thin cirrus overlaps lower-level water clouds in high spectral resolution infrared radiance measurements. We will present results from radiative transfer modeling of multi-layered cloud systems in the infrared window region using a set of approximately 18 microwindows at wavelengths between 8 and 12 µm. Ice cloud microphysical models are based on in-situ measurements of both particle size distributions from polar, midlatitude, and tropical cirrus clouds. From these new microphysical cirrus models, we derive scattering models derived from theoretical calculations using ray tracing, finite difference time domain (FDTD), and other approaches such as the stretched scattering potential method (SSPM). Ultimately, the feasibility of detecting multi-layered clouds will be inferred from comparison of measured radiances with those from a radiative transfer model. We will compare our modeled results to measurements made by the University of Wisconsin High-resolution Interferometer Sounder during the SUCCESS field experiment of 1996.