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We aim to delve into the characteristics of endogenous endophthalmitis caused by Klebsiella pneumoniae, focusing on the clinical manifestations, systemic risk factors, sources of the microorganism, and treatment outcomes among patients in our clinical series. All patients exhibited the classic symptoms of eye pain, redness, and reduced vision, with discernible risk factors of diabetes mellitus. In all cases, there were identifiable sources of bacteremia, most prominently liver abscess, followed by pneumonia and hand abscess. From the vitreous, positive cultures were obtained in all five cases, and all patients demonstrated bacteremia with positive Klebsiella growth. Late-stage unsalvageable presentations were observed in three cases, necessitating evisceration of the eye. One patient succumbed to sepsis with multiorgan failure. Despite prompt management of Klebsiella endophthalmitis, all patients in this clinical series had unfavorable visual or survival outcomes. Prevention in the form of good systemic control in patients with diabetes is crucial to prevent this life and sight-threatening complication.