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Abstract Medical adhesives are vital for securing wearable sensors, wound dressings, and critical medical devices. These adhesives must balance strong adhesion with patient comfort, especially when used over extended periods. Adhesives that maintain their efficacy for more than two weeks are essential for continuous monitoring devices, as they enhance diagnostic accuracy and reduce dressing changes, minimizing patient discomfort and infection risk. However, current long-wear adhesives often use aggressive acrylics that can cause skin injuries. To overcome these limitations, we developed an advanced ThermoTape offering temperature-responsive properties with a polyurethane backing for more than 14 days of wear. A double transfer coating process fabricated PU-ThermoTape, with surface morphology characterized using Atomic Force Microscopy. Differential Scanning Calorimetry and thermography determined the optimal removal window. Peeling strength tests were conducted at room and elevated temperatures to assess performance. In vitro, PU-ThermoTape displayed an average peeling strength of 0.3 N/mm at 25 °C, decreasing by 75% when heated to 45°C, with an optimal removal window of approximately 2.5 minutes. The tape demonstrated excellent skin conformity with its polyurethane backing. In a 14-day wearability study with seven volunteers, PU-ThermoTape outperformed Tegaderm, maintaining temperature-responsiveness and allowing unrestricted daily activities throughout. PU-ThermoTape provides robust adhesion, high skin conformity, and facilitates gentle removal after brief warming, positioning it as a versatile adhesive suitable for various applications with different duration requirements.