The number of instructional offerings in higher education that are online, blended, or web-enhanced, including courses and programs, continues to grow exponentially. Alongside the growth of e-learning, higher education has witnessed the explosion of cloud-based or Web 2.0 technologies, a term that refers to the vast array of socially oriented, free or nearly free, web-based tools, has represented a transition from institutionally-provided to freely available technology tools. This paper addresses the numerous teaching and learning opportunities and challenges that institutions face in adopting and implementing cloud-based technologies into their eLearning programs and provides a guide for forming implementation decisions. (Contains 3 tables.)