Learning environments have evolved rapidly in the past decade growing the encompass Learning Management Systems, rich digital content, and multiple forms of access including new mobile technologies. In the process students have moved further and further away from traditional classrooms where teachers have historically provided face-to-face learning content and supports. Digital information sources have vastly exceeded the capacity of any one content specialist but learning supports have been harder to establish in a decentralized education model. Communication methods have become moved to asynchronous types in the form of e-mail, texts, and discussion forums. This has left teachers with a serious disconnect that has not, as yet, been reconciled by technology or methodology. This indicates a gap which learning environments and teachers’ alike need to bridge before ubiquitous learning environments can fully achieve the goal of successfully meeting learner needs outside of the classroom paradigm.