Background: Virtual surgical planning (VSP), intraoperative cutting guides and stereolithographic models, provides the head and neck reconstructive surgeon with powerful tools for complex reconstruction planning. Despite its use in fibular osteocutaneous reconstruction, application to the scapular tip has not been as widely reported. Methods: From 2013 to 2014, four cases of either mandibular or maxillary reconstruction were completed with the scapular tip osseous free flap. All four cases underwent preoperative VSP with patient-specific guide design. Results: Patient-specific guides were generated for scapular tip harvest. Guide placement was improved using a stabilizing flange and bracket design. With minimal disruption of the overlying periosteum a wedge osteotomy was successfully implemented in one case. Conclusions: Unlike the fibula and iliac crest donor sites, the scapular tip has overlying muscle attachments that make intraoperative osteotomies challenging. Attention to key aspects of scapular anatomy, including the fibrous tip and extensive overlying muscle, permits effective guide design. Level of evidence: 4.