Ubiquitous computing has long pursued Weiser's vision of technologies that "disappear" into everyday life. As wearable health systems advance, they increasingly substitute for rather than scaffold users' judgment, yet the long-term consequences remain underexplored. We report an eight-year, five-wave longitudinal interview study from 2017 to 2025 with 37 patients with diabetes, complemented by interviews with 15 clinicians, designers, and vendors. Across three technological generations including glucometers, continuous glucose monitoring, and predictive and automated insulin delivery systems, we identify a novel user state, continued use with cognitive disengagement. In this state, devices remain in use but active interpretation and questioning recede, leaving users to respond only to alarms. This state emerges from functional expansion, delegation of interpretive authority, and information fatigue, and is reinforced by clinical prioritization, information compression, and automation. It results in less frequent independent health judgment and a shift from understanding to responding. We argue that future diabetes computing systems should reduce unnecessary cognitive work while preserving users' opportunities to interpret, contextualize, and question system outputs.

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