A: At Oates Insurance, we recommend enrolling in Medicare during your Initial Enrollment Period, which begins three months before the month you turn 65, includes your birthday month, and extends three months after. This seven-month window is crucial to avoid late enrollment penalties and ensure your coverage starts on time. If you are still working and have employer-sponsored health insurance, you may qualify for a Special Enrollment Period when that coverage ends. Given our expertise in Medicare and personalized, in-person consultations, we can guide you through the enrollment process to help you make informed decisions tailored to your specific needs and circumstances. Contact Oates Insurance early to schedule a review and secure the best coverage as you approach 65.