Background: Uncontrolled diabetes is a serious medical condition that can lead to various complications, including ulcerated boils on the legs. These complications occur due to the neurovascular complications associated with diabetes. Staphylococcus aureus and Streptococcus agalactiae are frequently encountered pathogens, and polymicrobial infections are prevalent. Antibiotic treatment targets commonly isolated organisms by considering local resistance profiles, patient preferences, and infection severity. Mild to moderate infections may be managed with oral antibiotics, whereas severe cases require intravenous therapy. Severe or persistent cases may require surgical intervention and specialized, multidisciplinary wound care. Case Presentation: In this case report, we present the case of a patient who presented with an ulcerated boil of the left leg that initially appeared as a pimple a week ago. The patient had been diagnosed with type 2 diabetes mellitus (T2DM) but had discontinued medication a year ago due to potential side effects. Conclusion: This case emphasizes the importance of maintaining proper diabetes management and adherence to medication to prevent complications, such as ulcerated boils on the legs.