Abstract:Researchers have long recognized the socio-technical gaps in personal tracking research, where machines can never fully model the complexity of human behavior, making it only able to produce basic rule-based outputs or "black-box" results that lack clear explanations. Real-world deployments rely on experts for this complex translation from sparse data to meaningful insights. In this study, we consider this translation process from data to insights by experts as "sensemaking" and explore how HCI researchers can support it through Vital Insight, an evidence-based 'sensemaking' system that combines direct representation and indirect inference through visualization and Large Language Models. We evaluate Vital Insight in user testing sessions with 14 experts in multi-modal tracking, synthesize design implications, and develop an expert sensemaking model where they iteratively move between direct data representations and AI-supported inferences to explore, retrieve, question, and validate insights.