Sixty-five comes with a calendar most people never see: one window to enroll without a penalty, a different set of rules if you're still working, and a later window to change your mind. Here's the whole thing in order — who's enrolled automatically, how to apply if you're not, and the two penalties worth planning around.
Required disclosures: Smooth Health Solutions is not connected with or endorsed by the United States government or the federal Medicare program. We do not offer every plan available in your area. Currently we represent 0–78 organizations which offer 0–2,613 products in your area. The exact number of organizations and products depends on your ZIP code, county, and plan year. Please contact Medicare.gov, 1‑800‑MEDICARE, or your local State Health Insurance Assistance Program (SHIP) to get information on all of your options. This page is educational, not a recommendation of any specific plan.
If you're already receiving Social Security (or Railroad Retirement) benefits when you turn 65, enrollment is automatic. Parts A and B start the first day of your birthday month and the red-white-and-blue card shows up in the mail about three months ahead. Your only real decision is whether to keep Part B (almost everyone should — declining it while not covered by a large employer starts the penalty clock) and what to add around Original Medicare.
Everyone else — still working, or simply not collecting Social Security yet — applies. That's most people these days, and it's genuinely quick.
All three run through Social Security — Medicare doesn't take its own applications. All three are free.
Usually 10–20 minutes. You'll need your basic identity details and, if you have one, your my Social Security account login. You can apply for Medicare only — you do not have to start your retirement benefits at the same time, and most people shouldn't conflate the two decisions.
TTY 1‑800‑325‑0778. Say you want to file for Medicare; they'll take it by phone or book an appointment to finish. Yes, this fully counts — "can you apply for Medicare over the phone" is one of the most-asked questions there is, and the answer is simply yes.
Call the same number first to make an appointment rather than walking in. Worth it when your situation has wrinkles — mixed work history, immigration timing, disability transition — and you want a human working the file with you.
The Initial Enrollment Period runs the three months before your birthday month, your birthday month, and the three months after. The timing detail that matters: enroll in the three months before your birthday month and coverage starts on the first of your birthday month — enroll during or after it and your start date slips later. If you want no gap, apply early in the window.
Covered by a current employer's plan (yours or your spouse's) at an employer with 20 or more employees? You can usually delay Part B penalty-free and, when that job or coverage ends, an 8-month Special Enrollment Period opens to pick it up cleanly. Under 20 employees, Medicare generally becomes primary at 65 whether you enrolled or not — meaning claims can be paid as if Medicare existed, and skipping enrollment leaves you effectively uninsured. Plenty of people get this answer from a coworker instead of someone licensed; it's the single costliest guess in Medicare. COBRA and retiree coverage do not count as active employment for this rule.
Both are lifelong, not one-time: Part B premiums rise 10% for each full 12 months you could have had it but didn't, and Part D adds roughly 1% of the national base premium per month without creditable drug coverage. Run your own numbers in the penalty calculator — seeing your own figure is usually what settles the "I'll deal with it later" debate.
Original Medicare alone has no out-of-pocket maximum and no drug coverage — so the next decision is the shape of the rest: Advantage or Medigap, plus drug coverage either way. That decision has its own one-way door, and it deserves more than an afternoon. Track where your application stands at check your application status.
Twenty minutes with a licensed agent and you'll know which dates are yours, what needs a decision now, and what you can leave alone. Or have the windows sent to you before they open.
No cost. No obligation to enroll. We do not offer every plan available in your area.
The decisions that follow the application:
Important: Smooth Health Solutions is not connected with or endorsed by the United States government or the federal Medicare program. We do not offer every plan available in your area. Currently we represent 0–78 organizations which offer 0–2,613 products in your area. The exact number of organizations and products depends on your ZIP code, county, and plan year. Please contact Medicare.gov, 1‑800‑MEDICARE (1‑800‑633‑4227; TTY 1‑877‑486‑2048), or your local State Health Insurance Assistance Program (SHIP) to get information on all of your options. This page is for general education, reflects 2026 amounts published by CMS, and is not a complete description of benefits or a recommendation of any specific plan. Enrollment cannot be guaranteed until an application is accepted by the applicable insurance company or program.