Background: In the face of rapid technological advances in computational cytology including artificial intelligence (AI), optimization of its application to clinical practice would benefit from reflection on the lessons learned from the decadeslong journey in the development of computer-assisted Pap test screening. Summary: The initial driving force for automated screening in cytology was the overwhelming number of Pap tests requiring manual screening, leading to workflow backlogs and incorrect diagnoses. Several companies invested resources to address these concerns utilizing different specimen processing techniques and imaging systems. However, not all companies were commercially prosperous. Successful implementation of this new technology required viable use cases, improved clinical outcomes, and an acceptable means of integration into the daily workflow of cytopathology laboratories. Several factors including supply and demand, Food and Drug Administration (FDA) oversight, reimbursement, overcoming learning curves and workflow changes associated with the adoption of new technology, and cytologist apprehension, played a significant role in either promoting or preventing the widespread adoption of automated screening technologies. Key Messages: Any change in health care, particularly those involving new technology that impacts clinical workflow, is bound to have its successes and failures. However, perseverance through learning curves, optimizing workflow processes, improvements in diagnostic accuracy, and regulatory and financial approval can facilitate widespread adoption of these technologies. Given their history with successfully implementing automated Pap test screening, cytologists are uniquely positioned to not only help with the development of AI technology for other areas of pathology, but also to guide how they are utilized, regulated, and managed.