Objective: To retrospectively analyze local and systemic factors that resulted in the short-term tooth loss that were previously assigned a favorable prognosis in patients who were seen and treated at the University of California San Francisco (UCSF) School of Dentistry over an observational five-year period.Materials and Methods: This retrospective study included the records of patients who had a minimum of two dental exams at least twelve months apart at the UCSF School of Dentistry over a 5 year period. This study investigated extracted teeth with an initially favorable periodontal prognosis that were then divided into one of four categories based on the reason for extraction: caries, periodontal disease, endodontic reason, or fracture. Patient and tooth related factors associated with the extracted teeth were recorded: crown-to-root ratio, initial pocket depth, initial periodontal diagnosis, maintenance interval, presence of existing restoration, furcation involvement, and systemic conditions. Data analysis was performed using a linear mixed model. Results: A total of 50 patients with 111 teeth met the inclusion criteria for this study. A higher odds ratio (OR) for tooth loss due to caries, endodontic reason, and fracture were found in teeth with a history of root canal treatment with an OR of 3.61, 3.86, and 2.52, respectively. For tooth loss due to periodontal disease, higher ORs were found in patients who were on anti-depressants (OR= 4.28) and patients who had an initial diagnosis of Stage III/IV periodontitis (OR= 2.66). In addition, teeth with initial probing depths ≥ 5 mm (OR= 4.32) and with furcation involvement (OR= 1.93) also showed a higher OR for tooth loss due to periodontal disease. Conclusion: Within the limitations of this study, previously root-canal treated teeth present a higher OR for early loss due to caries, recurrent endodontic lesions, or fracture. In addition, patients with anti-depressant medication use, sporadic maintenance, initial probing depths ≥5 mm, and furcation involvement represent significantly higher OR of tooth loss due to periodontal disease even for initially favorable teeth.