Anterior cruciate ligament reconstruction (ACLR) is one of the most frequently performed procedures in orthopaedic sports medicine. Intraoperative challenges related to graft procurement, graft preparation, and graft placement are common. Frequently encountered difficulties include insufficient graft diameter and graft-tunnel length mismatches, whereas less frequent challenges may be encountered during graft harvest and handling. This article discusses these possible complications and the strategies for their prevention and management. For successful ACLR, clinicians must be prepared to address each of these potential sources of difficulty.