GlobePort, a nationwide adult-care business, offers its employees health insurance benefits using a variety of vendors. Each vendor has different medical/dental/life insurance plans with different application formalities. Two years back, GlobePort found it difficult to support all of these variations and decided to pursue business process outsourcing (BPO) of their benefits verification process and information systems updates. Recently there have been multiple complaints about issues faced by employees due to procedural and technological problems as a result of the outsourcing. Analysis of these complaints suggest that a knowledge sharing gap exists between GlobePort, its employees, the BPO provider and the insurance vendors. GlobePort needs to close this gap by adopting suitable knowledge management systems. Additionally, GlobePort is expanding its outsourcing arrangements to include several of their core business processes such as specialized adult-care tasks utilizing multiple vendors. This case asks the reader to select a set of knowledge management practices and collaboration technologies that can help GlobePort address their current employee complaints and support the challenges from the future expansion of outsourcing of their core adult-care processes.