Artificial Intelligence (AI) is poised to revolutionize healthcare deliver by becoming valuable tools to augment clinical decision making, optimize clinical workflows, facilitate patient interactions, and improve patient outcomes. Clinical decision-making involves considering various factors beyond the immediate data, such as the patient preferences, medical history, ethical considerations, and the healthcare setting/operational environment. AI algorithms need to be designed to incorporate this contextual information to ensure their recommendations align with real-world clinical practice. Translating AI enhanced healthcare technologies from the lab to the clinic, especially for military applications in expeditionary settings where resources may be limited, requires a unique synergy between engineers, clinicians, and military advisors. This presentation will explore the critical importance of interdisciplinary collaboration, highlighting the challenges and potential solutions in developing clinical AI applications for the military. Developing robust AI algorithms relies heavily on access to large, high-quality datasets. For example, in dental applications the datasets used to develop AI systems comprise of diverse data types including clinical records, radiographs, and intraoral images for diagnostics and fabrication of dental appliances. Processing this heterogeneous data presents significant challenges due to data variability, data scarcity, data privacy and the potential of incomplete datasets. An associated challenge includes data sharing between DHA and collaborators in academia or industry. Leveraging opportunities to facilitate collaborations where data sharing is restricted will be critical to develop novel AI systems. The U.S. Army Artificial Intelligence Institute (A2I2) has a development environment that enables collaborations with leading AI experts in the U.S. to solve Army problems related to Expeditionary Maneuver and Air/Ground Reconnaissance. Recently, the A2I2 development environment was utilized by researchers at the U.S Army Institute of Surgical Research to develop Synthetic Dental Radiographs. The dental research officers at USAISR can leverage their clinical knowledge and experience to integrate with technology development teams to advance development of AI systems to optimize dentistry in garrison and augment expeditionary dentistry. Military dental research is an opportunity to advance Military Dentistry, but the technology, techniques and knowledge gained by developing these AI systems can translate to other clinical applications throughout the military healthcare system. The algorithms and techniques developed for Dental AI systems can serve as a platform to advance AI development to augment clinical decision making, interpret medical imaging, advance medical robotics, and integrate AI systems with virtual health capabilities. The co-presenters have collaborated to develop AI enhanced portable medical devices for expeditionary use and dental AI systems. A point of discussion among the presenters is how can differences in clinical judgement among healthcare providers (end-user) impact the development, testing and validation of clinical AI systems. While AI excels at pattern recognition and data analysis, current technology cannot fully replicate or replace the clinical judgment of experienced healthcare providers. The impact of clinical judgement on development of AI systems is not well studied but is an important component to consider when implementing AI systems into expeditionary and clinical workflows.