--- title: "Turning 65: a Medicare checklist" description: "A step-by-step Medicare checklist: your enrollment window, employer coverage, the parts of Medicare and how penalties work." url: https://seniorchoicecare.com/medicare-advantage/turning-65-checklist/ updated: 2026-10-09 site: Senior Choice Care --- Medicare Advantage # Turning 65: a Medicare checklist 2027 plan year Talk a plan through with a licensed agent Free, no obligation, no pressure. Have your doctors and prescriptions nearby. [](#) TTY 711. Mon to Fri, 8 a.m. to 8 p.m. The mail starts arriving months early. This checklist strips it down to the handful of decisions that actually matter, and the dates that decide them. **We do not offer every plan available in your area.** Currently we represent a small number of insurance agencies and the plans they carry. Please contact Medicare.gov, 1-800-MEDICARE (TTY 1-877-486-2048), 24 hours a day / 7 days a week, or your local State Health Insurance Assistance Program (SHIP) to get information on all of your options. We are an independent information and referral resource. We are not connected with, endorsed by, or acting on behalf of the United States government, the Centers for Medicare & Medicaid Services, or the federal Medicare program. Calling a number on this page connects you with a licensed insurance agent or a third-party marketing partner. ## Know your enrollment window Your Initial Enrollment Period is a seven-month window: the three months before your birthday month, your birthday month, and the three months after it. For example, a birthday in June opens the window on March 1 and closes it on September 30. Signing up in the first three months generally gets coverage running on the first day of your birthday month. ## Check whether you are still covered by an employer **Still working, or covered by a spouse who is, at a company with 20 or more employees?** That active group coverage may let you delay Part B without a penalty. Confirm with the benefits office that the plan counts as creditable coverage, and get it in writing. **On retiree coverage, COBRA or a marketplace plan?** Those generally do not count. Enroll during your window to avoid a permanent late-enrollment penalty. ## Know what the parts are - **Part A, hospital insurance.** Usually premium-free for people who paid Medicare taxes for at least ten years. - **Part B, medical insurance.** Covers doctor visits, outpatient care and testing. It carries a standard monthly premium. - **Part C, Medicare Advantage.** A private plan that replaces the way Parts A and B are delivered and often includes drug coverage and extras. - **Part D, prescription drugs.** Either built into a Medicare Advantage plan or bought as a stand-alone plan alongside Original Medicare. ## Avoid the two penalties people regret **The Part B penalty** adds a percentage to your monthly premium for each full year you were eligible but did not enroll, and it stays for as long as you have Part B. **The Part D penalty** is calculated per uncovered month and is also permanent. Both are avoidable with a five-minute check of your dates. ## Then choose your shape of coverage Either Original Medicare with a supplement and a drug plan, or one Medicare Advantage plan that bundles it together. The trade-offs are laid out in our comparison guide, and a licensed agent can run the plans available at your ZIP code for you. ## Request a plan review Prefer not to call? Leave your name, phone number and ZIP code and a licensed insurance agent will reach out to compare the plans available where you live against the doctors and prescriptions you use. ## Keep reading - [**medicare advantage**](https://seniorchoicecare.com/medicare-advantage/) - [** vs original medicare**](https://seniorchoicecare.com/medicare-advantage/vs-original-medicare/) --- Canonical page: https://seniorchoicecare.com/medicare-advantage/turning-65-checklist/