Segmental maxillary osseodistraction is a proper method to close alveolar gaps in patients with clefts of lip, palate, and alveolus. The technique is mainly used in very wide clefts after failure of conventional bone grafting procedures. The aim of the study was to analyze problems that may occur during the distraction process. Patients with uncommon wide alveolar clefts or recurrent oronasal fistulas and patients with bilateral clefts of lip, plate, and alveolus and an additional vertical deficit of the posterior cleft segment underwent distraction procedures. The patients were subdivided according to the vector of distraction: linear (following the dental arch) and vertical. The devices for horizontal distraction were tooth-borne and manufactured to the specific clinical situation. For vertical distraction, standard devices were used. Of this sample, patients with complications occurring during or after surgery and during the distraction period were selected as the study participants. On the basis of the data collected on these complications, the need for additional bone grafting procedures was evaluated. Results suggest that modifications in preoperative planning and the construction of the distraction devices may be necessary to prevent unexpected problems in segmental maxillary distraction procedures. Considerations concerning the placement of distraction devices are discussed.