BACKGROUND The extraction of maxillary impacted teeth is a common procedure in oral surgery, frequently complicated by oroantral communications. For less-experienced clinicians, accurately assessing the difficulty and associated risks of maxillary third molar extractions remain a significant challenge. CASE SUMMARY We present a case involving disparate outcomes following bilateral extraction of maxillary third molars. Using cone-beam computed tomography and three-dimensional software, we conducted a digital assessment of the factors contributing to extraction difficulty and risk, controlling for potential confounders. Key variables analyzed included alveolar bone volume, bone quality, crown-root angulation, and maxillary sinus mucosal thickness. Additionally, we introduce the novel concept of "tegmen bone" to quantitatively evaluate the bone mass between the teeth and the maxillary sinus. This unique case, with differing outcomes on opposite sides of the same patient, provided an opportunity to minimize extraneous variables and focus on the local anatomical factors influencing the procedures, thereby improving the precision of our analysis. CONCLUSION This case highlights the potential utility of predictive analysis in guiding the management of complex tooth extractions.