Purpose Ischaemic complications of the nipple-areola complex (NAC) after breast reduction surgery can have serious aesthetic, functional, and psychological effects, particularly in patients with grade 3 ptosis. Indocyanine green (ICG) angiography combined with SPY imaging enables intraoperative monitoring of skin perfusion, potentially reducing ischaemic complications through real-time identification and correction. Methodology We describe two cases of obese patients (BMI 33 and 35) with grade 3 breast ptosis who underwent bilateral reduction mammaplasty. Intravascular ICG and SPY system were employed to monitor NAC perfusion, enabling intraoperative correction of vascular compromise. Results The average reduction volume was 912g. In both cases, the SPY system detected inadequate NAC perfusion following pedicle inset. After further mobilisation and reducing pedicle angulation, repeat perfusion checks demonstrated marked improvement. Additionally, to address venous congestion, fenestration of the NAC was performed using heparinised saline-soaked gauze, along with negative pressure dressings. Both patients had satisfactory wound healing at two-week follow-up. Conclusion Patients with grade 3 ptosis and high BMI are at elevated risk for NAC ischaemia during breast reduction mammaplasty. Intraoperative monitoring using ICG and the SPY system facilitates real-time correction of pedicle positioning, optimising perfusion and preventing complications. This technique may improve both short- and long-term outcomes by reducing wound-related morbidity.