Urinary tract infection (UTI) is caused by bacteria growing in urine and affect kidneys, bladder, ureters, and urethra. Women with diabetes are at high risk of developing UTI. This is a case of a 60-year-old postmenopausal woman with uncontrolled type-I diabetes mellitus and hypertension, who presented with an acute onset of dysuria, burning micturition, and increased frequency. This case highlights the shortfall in the preliminary management plan of performing imperative clinical laboratory investigations including urine detailed report (DR), urine culture and sensitivity(C/S), and plasma glucose testing to initiate antimicrobial treatment. UTI requires to be treated precisely in diabetic patients with the help of a comprehensive diagnosis for signs of dysuria, frequent urination, and pelvic pain. The treatment of UTIs should always begin with culture and sensitivity analysis while the patient is symptomatic, to initiate antimicrobial treatment. Comorbidities should be managed appropriately during treatment to achieve desired therapeutic outcomes.