This article describes techniques used to synthesize headphone-presented stimuli that simulate the ear-canal waveforms produced by free-field sources. The stimulus synthesis techniques involve measurement of each subject's free-field-to-eardrum transfer functions for sources at a large number of locations in free field, and measurement of headphone-to-eardrum transfer functions with the subject wearing headphones. Digital filters are then constructed from the transfer function measurements, and stimuli are passed through these digital filters. Transfer function data from ten subjects and 144 source positions are described in this article, along with estimates of the various sources of error in the measurements. The free-field-to-eardrum transfer function data are consistent with comparable data reported elsewhere in the literature. A comparison of ear-canal waveforms produced by free-field sources with ear-canal waveforms produced by headphone-presented simulations shows that the simulations duplicate free-field waveforms within a few dB of magnitude and a few degrees of phase at frequencies up to 14 kHz.