Purpose Postoperative wound complications, including SSIs, remain a major cause of mortality after hepatobiliary (HPB) surgery. Visual assessment is insensitive to early healing impairment. Infrared thermography (IRT) provides non-invasive, real-time evaluation of skin temperature and perfusion. This preliminary study characterizes thermographic healing patterns after open and laparoscopic HPB surgery. Methodology A prospective observational study included 40 patients undergoing HPB surgery (20 open, 20 laparoscopic). High-resolution thermographic images and standard photographs were obtained preoperatively and on postoperative days (POD) 1-3 under standardized conditions using the FLIR T1020 system. Wound and periwound regions of interest were analyzed with custom software to assess mean temperature, temperature gradients, and cold spots (≥1.5°C below mean wound temperature). Clinical and laboratory data were collected for correlation. Results Open wounds showed central and lateral hypothermic zones on POD1, consistent with early inflammatory-phase hypoperfusion. Progressive thermal normalization by POD3 reflected angiogenesis with critical hypoperfusion-prone areas at incision edges, suture convergence, and the inferior wound pole. Laparoscopic wounds showed faster thermal recovery. A periwound “white halo” appeared by POD2, particularly around periumbilical trocar sites, corresponding to robust microvascular perfusion within DIEA territories. Lateral trocar sites showed cooler, irregular margins. Infected wounds showed delayed or absent thermal normalization, with persistent cold spots and surrounding hyperthermia preceding clinical signs of SSI. Conclusion IRT wound dynamics reflect underlying microcirculatory processes and differ reproducibly between open and laparoscopic approaches. A 10-item Thermal Healing Scale was developed for point-of-care assessment. IRT provides objective insight into postoperative wound healing and may improve early detection of SSIs.