Selecting potential recipient vessel options for free flap anastomosis is an important consideration in microsurgical breast and chest wall reconstruction. In these settings, the most common comprise the internal mammary and thoracodorsal vessels, although alternative anastomotic sites have also been described. On occasion, consideration of these alternatives becomes a necessity. The use of five separate recipient vessels is highlighted in a unique case of recurrent locally advanced breast cancer requiring multiple complex reconstructions using free tissue transfer. A 56-year-old lady presented for delayed breast reconstruction one year after radical mastectomy for locally advanced lobular breast cancer. Despite wide resections, local chest-wall recurrence five times necessitated five microsurgical reconstructions, using separate recipient pedicles: internal mammary vessels, thoracodorsal vessels, serratus branch of thoracodorsal vessels, intercostal vessels and thoracoacromial vessels. All flaps survived completely, without donor or recipient complications. There has not been a subsequent recurrence at 6 months since last reconstruction. The purpose of this report is to present the first reported case of microsurgical chest wall reconstruction using five separate free flaps requiring anastomosis to multiple recipient vessels for anterior chest wall coverage, to present a literature-based and clinical review of the regional vascular anatomy of the anterior chest wall, and to present an operative approach algorithm. In such complex cases, this understanding can facilitate a streamlined approach to management.