Animal signals experience selection for detectability, which is determined in large part by the signal transmission properties of the habitat. Understanding the ecological context in which communication takes place is therefore critical to understanding selection on the form of communication signals. In order to determine the influence of environmental heterogeneity on signal transmission, we focus on a wolf spider species native to central Florida, Schizocosa floridana, in which males court females using a substrate-borne vibratory song. We test the hypothesis that S. floridana is a substrate specialist by (i) assessing substrate use by females and males in the field, (ii) quantifying substrate-specific vibratory signal transmission in the laboratory, and (iii) determining substrate-specific mating success in the laboratory. We predict a priori that (a) S. floridana restricts its signaling to oak litter, (b) oak litter best transmits their vibratory signal, and (c) S. floridana mates most readily on oak litter. We find that S. floridana is almost exclusively found on oak litter, which was found to attenuate vibratory courtship signals the least. Spiders mated with equal frequency on oak and pine, but did not mate at all on sand. Additionally, we describe how S. floridana song contains a novel component, chirps, which attenuate more strongly than its other display components on pine and sand, but not on oak, suggesting that the ways in which the environment relaxes restrictions on signal form may be as important as the ways in which it imposes them.