Improved long-wavelength transmission and supercontinuum (SC) generation is demonstrated by antireflective (AR) nanoimprinting and tapering of chalcogenide photonic crystal fibers (PCFs). Using a SC source input spanning from 1 to 4.2 μm, the total transmission of a 15 μm core diameter PCF was improved from ∼53% to ∼74% by nanoimprinting of AR structures on both input and output facets of the fiber. Through a combined effect of reduced reflection and redshifting of the spectrum to 5 μm, the relative transmission of light >3.5 μm in the same fiber was increased by 60.2%. Further extension of the spectrum to 8 μm was achieved using tapered fibers. The spectral broadening dynamics and output power were investigated using different taper parameters and pulse repetition rates.