Acute exacerbations of chronic periapical pathology require prompt surgical or endodontic intervention, supported by pharmacotherapy. The role of analgesic selection, escalation, and rotation in acute dental pain remains underexplored. A 39-year-old male dentist with a 27-year history of trauma to the lower left central incisor presented with acute pain of three hours' duration. The tooth was non-vital with a stable periapical granuloma documented for over 15 years. Self-medication began with paracetamol, escalating to ibuprofen, aceclofenac, and etoricoxib, when pain worsened. Amoxicillin and metronidazole were also taken for infection control. On day three, endodontic access without anesthesia yielded minimal pus drainage but immediate pain relief. The canal was initially left open, then medicated with calcium hydroxide, and finally obturated with gutta-percha and zinc oxide-eugenol sealer. Three years of follow-up showed no recurrence. This case demonstrates symptom-driven analgesic escalation and de-escalation in an informed patient and raises the concept of analgesic rotation for reducing cumulative toxicity. While this may be relevant in chronic pain management, its role in acute odontogenic pain is limited, especially for agents with shared adverse profiles such as non-steroidal anti-inflammatory drugs (NSAIDs). Timely endodontic intervention remains the cornerstone of treatment for acute periapical abscesses. Analgesic prescribing should be individualized and symptom-based rather than fixed-duration, with rotation considered selectively.