IMPORTANCE Reconstruction of oncologic or traumatic head and neck defects often requires complex planning of locoregional, pedicled, or interpolated flaps. In cases with a higher risk of flap failure, vascular delay with staged reconstruction can help improve tissue perfusion and increase chances of flap survival. An objective tool is needed to help guide reconstructive surgeons with the intraoperative decision to pursue vascular delay. OBJECTIVES To describe a pilot study using a novel application of a technique that quantifies and validates the benefit of the vascular delay procedure in locoregional flaps and to demonstrate a practical and broadly applicable technology that can be easily incorporated into intraoperative decision making and improve outcomes for high-risk flaps. DESIGN, SETTING, AND PARTICIPANTS A pilot study using intraoperative laser-assisted indocyanine green imaging measurements and fluorescence videos to objectively measure the benefit of vascular delay procedures in patients with head and neck defects and wound healing risk factors requiring locoregional flap reconstruction at an academic tertiary care center. MAIN OUTCOMES AND MEASURES Intraoperative laser-assisted indocyanine green imaging with video documentation and quantitative measurements was used to evaluate flap perfusion before a vascular delay procedure. Measurements were repeated after a 3-week vascular delay procedure. RESULTS Two patients were identified based on comorbid conditions that resulted in a higher risk of flap failure, as well as the need for a locoregional flap for reconstruction. At the initial elevation of the flap, quantitative results from flap imaging demonstrated low perfusion numbers and minimal fluorescence, suggesting poor tissue perfusion and increased likelihood of postoperative flap compromise or failure. Following a vascular delay of 3 weeks, repeat measurements were substantially improved. No wound healing issues were observed. CONCLUSIONS AND RELEVANCE This is the first study to date to quantitatively demonstrate the benefit of the vascular delay technique in patients with potential vascular compromise in locoregional head and neck flap reconstruction. Data obtained suggest that this technology can be used to guide intraoperative decision making in complicated reconstructions and help optimize patient outcomes. LEVEL OF EVIDENCE NA.