Traumatic or infective injury to the proximal interphalangeal joints (PIPJ) of the finger often results in a limited range of motion and hand function and are usually associated with chronic pain owing to inevitable osteoarthritic changes. Management of PIPJ injury can be challenging, and surgical options include prosthetic arthroplasty and arthrodesis. With the advent of microsurgery, the management option had expanded to include autologous joint transfers, allowing the replace of like-with-like reconstruction. We describe a series of 5 patients who received free vascularized toe joint transfers for PIPJ reconstruction. Patient demographics, co-morbidities, surgical details, and outcomes were recorded. All patients sustained their injury from acute trauma and received the toe joint transfer in a delayed fashion between 7-13 months after their initial injury. The toe joint was raised based on the 1st dorsal metatarsal artery and superficial dorsal vein. Options for recipient arteries included the 1st, 2nd and 3rd common digital arteries. The superficial dorsal vein was used as the recipient vein for all patients. The median post-operative inpatient stay was 5 days, with 1 patient requiring medicinal leech therapy. 1 patient subsequently underwent an amputation of the digit secondary to post-operative osteomyelitis. All other patients were satisfied with the functional outcome of the reconstruction, with minimal donor site morbidity. Current literature reflects a narrow but clear indication for free vascularized toe joint transfer in well-selected and motivated patients. This case series describes our experience, the sharp learning curve, and the pitfalls of the vascularized toe joint transfer.