Surgical sutures are widely used for closing wounds in skin. However, the monitoring of wound integrity and promoting tissue regeneration at the same time still remains a challenge. To address this, we developed a drug-releasing electronic suture system (DRESS) to monitor the suture integrity in real-time and enhance tissue regeneration by triggered drug release. DRESS was fabricated by using a single fiber with a core-shell structure consisting of a stretchable conductive fiber core and a thermoresponsive polymer shell containing drugs. The highly conductive fiber core acts as a strain sensor that enables continuous monitoring of suture strain with high sensitivity (a gauge factor of similar to 686) and mechanical durability (being able to endure more than 3000 stretching cycles). The thermoresponsive shell layer composed of flexible poly(vinyl alcohol) (PVA) grafted onto poly(N-isopropylacrylamide) (PNIPAm) facilitates on-demand drug release via Joule heating. The results of an in vitro scratch assay showed a 66% decrease in wound area upon heat-activation after 48 hours demonstrating the stimuli-responsive therapeutic efficacy of DRESS by promoting cell migration. Moreover, ex vivo testing on porcine skin demonstrated the applicability of DRESS as a electronic suture. The approach used for DRESS provides insight into multifunctional sutures and offers additional therapeutic and diagnostic options for clinical applications.