Microsoft Office SharePoint Server 2007 ("MOSS") is one of the fastest growing server products in the history of Microsoft. MOSS is a portal product that provides a full spectrum of collaboration and content management functionality. As powerful and popular as the solution offerings have become, however, the technology for the most part is still misunderstood and its complexity underestimated. This paper will discuss the MOSS technologies and the challenges and failed considerations in deployment and management. The paper will identify some key best practices with respect to monitoring and management of SharePoint and will identify gaps and market needs that the proven set of Azaleos remote monitoring and management service solutions can effectively bridge.