The clinician faces treatment planning challenges when patients present with generalized severe chronic periodontitis that may result in tooth loss. This article provides a treatment planning discussion along with approaches for treating such patients. It presents the clinical question: What is the best means for approaching treatment planning in a patient with severe periodontitis requiring extraction and replacement of some teeth? Two treatment approaches are discussed—a reconstructive approach versus an adaptive one—both of which have an end goal of achieving periodontal health and occlusal stability, and each has its own advantages and disadvantages. In conclusion, utilizing a global prognostic approach will assist clinicians anticipate the eventual restorative needs of patients and prescribe customized periodontal and restorative therapies that best address those needs.