Safer human-robot interactions mandate the adoption of proprioceptive actuation. Strain sensors can detect the deformation of tools and devices in unstructured and capricious environments. However, such sensor integration in surgical/clinical settings is challenging due to confined spaces, structural complexity, and performance losses of tools and devices. Herein, we report a highly stretchable skin-like strain sensor based on a silver nanowire (AgNW) layer and hydrogel substrate. Our facile fabrication method utilizes thermal annealing to modulate the gauge factor (GF) by forming multidimensional wrinkles and a layered conductive network. The developed AgNW-hydrogel (AGel) sensors sustain and exhibit a strain-sensitive profile (max. GF = similar to 70) with high stretchability (200%). Due to its conformability, the sensor demonstrates efficacy in integration and motion monitoring with minimal mechanical constraints. We provide contextual cognizance of tooltip during a transoral procedure by incorporating AGel sensors and showing the fabrication methodology's versatility by developing a hybrid self-sensing actuator with real-time performance feedback.