This case study systematically assessed diverse approaches to sinus augmentation in the presence of sinus pathology. Three patients were carefully selected and categorized as pseudocyst (PsC) (type 1), mucous retention cyst (MRC) smaller than 20 mm (type 2), and MRC larger than 20 mm in size (type 3). All patients underwent sinus augmentation procedures, with each case utilizing a unique surgical approach. Spontaneous drainage was performed for the patient with PsC (type 1), followed by uncomplicated sinus augmentation. For the patient with an MRC smaller than 20 mm (type 2), aspiration of the cyst contents preceded sinus augmentation. Conversely, the patient with a larger MRC (type 3) underwent cyst enucleation followed by sinus augmentation after complete recovery of the sinus membrane. No complications were noted in any of the cases, and follow-up revealed stable implant installation at the site of sinus augmentation. Within the constraints of this study, the choice of surgical procedure, whether involving spontaneous drainage, aspiration, or enucleation, should be guided by an anticipated pathologic diagnosis and the size of the sinus cyst. This informed approach empowers clinicians to make well-informed decisions for the best possible outcomes and sustained results. Overall, this study offers valuable insights for clinicians seeking to optimize sinus augmentation procedures in the presence of sinus pathology.