Gartner analyst Jeffrey Mann called SharePoint a tool that people are required to use, not one they want to use. This is because, in spite of its market dominance (66% market share, according to Microsoft), users still face challenges with external collaboration and mobile access. Hightail allows users to connect their SharePoint content to the cloud and remove key obstacles posed by large file sizes and enterprise firewalls. This paper provides detail on how users can access SharePoint content using Hightail and the benefits to the company in the form of greater collaboration and productivity.