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Managing type 1 diabetes mellitus (T1DM) in elderly patients with multiple comorbidities presents significant challenges, particularly when complicated by persistent glycemic variability, severe hypoglycemia, and hypoglycemia unawareness. We present a 72-year-old Saudi male with T1DM, ischemic heart disease, hypertension, hypothyroidism, and peripheral neuropathy who was transitioned from multiple daily injections to insulin pump therapy. Prior to intervention, he had frequent severe hypoglycemia and elevated glycated hemoglobin (HbA1c) levels (9.4%, 8.8%). Following the initiation of hybrid closed-loop insulin pump therapy, glycemic control improved (HbA1c 7.7%), and hypoglycemia episodes decreased. However, a language barrier led to a critical insulin dosing error and hospitalization. This case highlights both the benefits and potential risks of insulin pump use in elderly patients. It underscores the importance of addressing language barriers, providing individualized education, and involving caregivers to reduce adverse outcomes. The case adds to the limited data on advanced diabetes technology in the elderly with complex comorbidities. Insulin pump therapy can be effective in elderly patients with T1DM and multiple comorbidities when personalized support and appropriate safeguards are implemented.