This chapter introduces an assessment rubric for virtual world learning environments (VWLEs) built from proven principles of user experience design, instructional design, interface design, learning theory, technical communication, instructional systems design (ISD), and VIE motivation theory. Titled the “CIMPLe System,” this rubric captures the ways that context, interactivity, motivation, presence, and cognitive load weave together to form a successful VWLE. The CIMPLe System offers an advance in how educators can assess the quality and predict the success of the VWLEs that they build. The holistic approach achieved in the CIMPLe System arises from the multidisciplinary approach represented in the tool. As designers consider what to build into the environment, they can refer to the CIMPLe System as a checklist to ensure that the environment meets the needs that the cross-disciplinary theory suggests are necessary.