A growing number of stakeholders argue for the use of second language (L2) speaking assessments that measure the ability to orally communicate in real time. A Web-based virtual environment (VE) that allows live voice communication among individuals may have potential for aiding in delivering such assessments. While off-the-shelf voice communication VEs, such as Second Life, have been used for language learning and to a much lesser extent, language assessment, a very limited number of such environments have been designed with the explicit aim of aiding in assessing L2 oral communication. Moreover, test developers who desire to build such a VE have little theoretical basis to guide them. This conceptual article fills this void by discussing some of the theoretical issues that were considered when the researchers built a VE to help deliver L2 oral communication assessments.