After a prior failed adoption, ComprehensiveCare plans for a second attempt in adopting Electronic Health Records. The owner-physicians on the board of directors have replaced the administrator due in part to the missteps of the prior adoption. William Shoemaker, the new administrator, must grapple with several important decisions to provide the highest likelihood of success for adopting the large-scale system. He must decide how the organization should choose the new system, the extent to which the system should be customized to their organization's idiosyncrasies, who should be responsible for tactical decisions in the customizations that are planned, what role consultants should play for their small to medium enterprise, how training should be accomplished, and finally how the implementation should be scheduled. This is the second case in a series of three cases concerning ComprehensiveCare's adoption of Electronic Health Records. This case challenges readers to make decisions based on the organizational context. Part two, provided in the teaching notes, updates readers on decisions made by the board and provides readers the opportunity to think critically about the potential ramifications of those decisions. This case provides a context that would be most relevant in a graduate level IS management course, an undergraduate fundamentals course, or a project management course. [For the first case in the series, see EJ1164216. For the final case, see EJ1164345.]