Commercial truck driving is an essential part of the national supply chain but one that adversely affects the environment. The purpose of this study is to determine the influence of the potential environmental benefits, among other factors, on continued use of bypass systems that can be discontinued at any time by a driver. The results from our study show that (1) economic benefits and industry pressures positively influence drivers’ use of bypass systems but (2) the environmental benefits of the technology do not, even though system vendors and state transportation agencies emphasize these benefits of the technology. Based on these findings, we conclude that sustainable information systems can be a viable option in a business context if usage leads to economic benefits. Our results and conclusions support the U.S. Environmental Protection Agency’s differentiation of public policy versus business perspectives on sustainable technology.