Vehicle-to-vehicle (V2V) communication using Dedicated Short Range Communications (DSRC) technology promises to help drastically reduce vehicle collisions. DSRC allows vehicles in a highly mobile and complex network to send and receive safety messages with more reliability and lower latency compared with other wireless technologies used for automotive communications. However, there are many factors that could cause a safety-critical automotive application to become unreliable due to communication failures. While the reliability of V2V communication has been a subject of study by several researchers, there are still open questions regarding how the placement of the DSRC devices (inside or outside the host vehicle), the vehicle’s interior elements and the differences in altitude can affect the V2V communications. This article provides experimental testing data and analyses in order to quantify the impacts of relative vehicle speeds, altitude differences between vehicles, and interior obstacles on V2V communication range and reliability for opposite traffic, in both city and highway environments. We discuss how these results can adversely affect the design parameters of safety critical applications by considering the V2V application “Safe Pass Advisory” on two-lane rural highways.