This case study examines the efforts of a mid-tier, cabinet-level state agency to transform its constituency services to be more effective using information technology. The agency, based in a rural Midwestern state, faced increased scrutiny to raise accuracy, lower wait times, decrease expenditures, increase constituency satisfaction, and expand services to the state. To meet these challenges, the agency conducted a series of meetings to determine best possible opportunities for change and decided that technology solutions, which supported their business vision of the future, would be the foundation for that change. Redesigning core organizational processes—using several technologies such as e-commerce, content management system, data warehousing, and mobile technologies—would revolutionize how the agency delivers these services to its constituency. Along the way, agency encountered several challenges such as staff turnover, leadership issues, outsourcing issues, and implementation issues. At the heart of their experience lie four theories: the technology adoption model, task–technology fit model, Delone–McLean model of information systems success, and Leavitt’s model of organizational change. This case will not only examine the academic issues surrounding the aforementioned theories, but will also discuss how the agency navigated through real-world issues to meet these challenges. By increasing the quality and quantity of information that governmental bodies provide “Joe Citizen,” our populations are able to have opportunities to be more self-sufficient and are able to hold our public trust more accountable and responsive to the needs of an ever-growing, ever-changing society at large.