First, the Window That Governs Everything

Your Initial Enrollment Period (IEP) is seven months long: the three months before your birthday month, your birthday month, and the three months after. Enroll during the first three months and coverage begins the first day of your birthday month - no gap. (If your birthday falls on the 1st, everything shifts one month earlier.)

The Month-by-Month Checklist

6 months out: Get oriented

  • Confirm whether you'll be retired or still working at 65 - this single fact determines your entire path (see below).
  • If you're already receiving Social Security benefits, you'll be enrolled in Parts A and B automatically; your card arrives by mail. Everyone else must actively enroll.
  • Start a folder: current insurance documents, medication list with dosages, your doctors' names.

4 months out: Learn the landscape

3 months out: Enroll in Medicare

  • Apply for Parts A and B at ssa.gov, by phone with Social Security, or at a local office. Applying in this window means day-one coverage in your birthday month.
  • Nearly everyone gets Part A premium-free (you or a spouse paid Medicare taxes for 10+ years). Part B carries the standard $202.90/month premium in 2026 , more at higher incomes.

2 months out: Choose your coverage

  • If you choose Medicare Advantage: compare plans in your county - verify your doctors are in-network, your drugs are on the formulary, and note each plan's out-of-pocket maximum.
  • If you choose the Medigap route: compare Plan G and Plan N rates from multiple carriers, and pick a standalone Part D plan matched to your medication list.
  • This is the step where a licensed agent saves you the most time and the most money: we run your doctors and drug list against every option and quote multiple carriers in one call, at no cost. 888-918-6920

1 month out: Execute

  • Submit your plan enrollment so everything is effective the first of your birthday month.
  • If you're going Medigap: your 6-month Medigap Open Enrollment Period begins the month you're 65 and enrolled in Part B. During this window, no carrier can turn you down or charge more for health history. This protection does not repeat later in most states - use it.

Birthday month: Verify

  • Cards in hand (Medicare card + plan card), premiums set up, first appointments confirmed as covered.
  • Note your plan's member portal and customer service line. Done.

Working Past 65: The Rules That Prevent Expensive Mistakes

Millions of people work past 65, and the rules here are where the costliest errors happen.

If your employer has 20 or more employees and you have group health coverage: you can delay Part B (and usually Part D) without penalty. Your employer plan pays primary. When you eventually retire or lose that coverage, an 8-month Special Enrollment Period lets you pick up Part B penalty-free, with a 2-month window for a Medicare Advantage or Part D plan. Many people in this situation still enroll in premium-free Part A at 65 - but note: if you contribute to an HSA, stop contributions before Part A begins, because Medicare enrollment ends HSA eligibility (and Part A can be backdated up to 6 months when you enroll later).

If your employer has fewer than 20 employees: Medicare generally pays primary at 65, and your group plan may pay very little until you enroll. Delaying Part B in this situation can leave you effectively uninsured for major costs. Enroll on time.

COBRA and retiree coverage do not count as active employer coverage for delaying Part B. Relying on COBRA past 65 is one of the most common - and most expensive - Medicare mistakes made.

The Penalties You're Avoiding by Following This Page

  • Part B late enrollment penalty: 10% added to your premium for each full 12-month period you could have had Part B but didn't - for life.
  • Part D late enrollment penalty: accrues after 63 days without creditable drug coverage, about 1% of the national base premium per month missed - for life. Even if you take no medications, a low-premium Part D plan blocks this penalty permanently.
  • The Medigap window: not a penalty, but a one-time protection. Missing your 6-month guaranteed-issue window can mean underwriting - and possible denial - if you want Medigap later.

What Medicare at 65 Actually Costs

Budget for: Part A ($0 for most), Part B ($202.90/month standard in 2026 ), plus either a Medicare Advantage premium (often $0–$30) or a Medigap premium (commonly $100–$250 for Plan G, varying by state and age) plus a Part D premium (~$34.50 average) . Higher incomes pay IRMAA surcharges on Parts B and D, based on your tax return from two years prior.

MegaCare's licensed agents run turning-65 enrollments every day: we confirm your dates, screen you for Extra Help and SNP eligibility, compare every route with your actual doctors and medications, and complete the enrollment with you on the phone - free.

Call 888-918-6920 TTY: 711, Mon-Fri 9am-6pm EST

Frequently Asked Questions

  • Do I get enrolled automatically at 65?

    Only if you're already receiving Social Security (or Railroad Retirement) benefits. Otherwise, you must actively enroll during your IEP.

  • Is Medicare free at 65?

    Part A is premium-free for most people. Part B, Part D, Medicare Advantage, and Medigap all carry costs. See the budget section above.

  • Can I keep my employer insurance and skip Medicare?

    If the employer has 20+ employees, yes - you can delay penalty-free while actively covered. Under 20 employees, generally no. Confirm your specific situation before your birthday.

  • What if I miss my Initial Enrollment Period?

    Without a Special Enrollment Period, you wait for the General Enrollment Period (January 1 - March 31), coverage starts the month after enrollment, and late penalties may apply. Details: Medicare Enrollment Periods.

  • When should I start this process?

    Six months before your 65th birthday is comfortable. Three months out is the minimum for a no-gap start.