The use of intramedullary nailing in the upper extremity is still controversial. Those who have experience with antegrade nailing have either great enthusiasm or strong criticism for the procedure. Criticism of the procedure is because of the trauma that can occur to the rotator cuff and possible impingement syndrome, which can occur after antegrade nail insertion. The technique of retrograde nail insertion with the unreamed humeral nail is described in detail. In a series of 190 retrograde nailings performed in a prospective multicenter study, the most frequent intraoperative problems were fissure or avulsion at the entry portal (n = 8; 4.2%) and secondary radial nerve palsy (n = 8; 4.2%). All radial nerve palsies recovered spontaneously. Sixty-eight patients were followed up until the fractures healed. There were five (7.4%) bone healing problems. Four of five could be solved with use of the unreamed humeral nail in a second operative procedure, whereas the fifth bone healing problem required plate osteosynthesis. Function of the shoulder and elbow joint was excellent in 89.7% and 88.3% of the patients, respectively. Retrograde humeral nailing is a safe and reliable procedure if done properly. It is a valuable stabilization technique for acute and pathologic fractures and for pseudarthrosis. Bone healing problems after unreamed humeral nailing must be analyzed individually, but they can be treated with the same implant in combination with cancellous bone grafts, reaming, additional hardware, or intrafragmentary compression.