Silver/silver halide-coated hollow-glass waveguides (HGWs) are capable of low-loss, broadband transmission at infrared wavelengths with the advantage of optical response tunability through alteration of a number of key design parameters. Generally, the design of circular HGWs has primarily involved optimization of the waveguide bore size and deposited film structure in order to obtain the desired optical response, with the waveguide bore size being held constant as a function of length. In this study, the effects of HGW structures consisting of linearly tapered inner diameters on the optical response at infrared wavelengths are theoretically and experimentally investigated. Theoretical analysis involving numerical ray optics methods accounting for the dynamic nature of bore size, and consequently light propagation, along the waveguide length is presented and compared to experimental results in order to gain a deeper understanding of these atypical HGW structures.