When do I sign up?

Your Initial Enrollment Period

Your first — and best — chance to enroll in Medicare is your Initial Enrollment Period. It’s built around your 65th birthday: the three months before your birthday month, your birthday month itself, and the three months after.

Enrolling in the months before your birthday month means your coverage is ready the moment you’re eligible. Enrolling later in the window means waiting on coverage you could already have had. If you know your birth month, I can tell you exactly where you stand in about a minute — call 1-888-808-8282 and ask.

Still working at 65?

If you’re still working at 65 and covered by your employer’s health plan, you may be able to delay parts of Medicare without penalty — but the rules hinge on details most people have never been told. Whether the employer’s plan counts depends on the size of the company. COBRA and retiree coverage generally do not count, which surprises a lot of people after it’s too late to fix.

This is the single most common situation where a five-minute phone call prevents a permanent penalty. If this is you, call 1-888-808-8282 before you decide anything.

When you retire: Special Enrollment Periods

When you eventually stop working or lose that employer coverage, a Special Enrollment Period opens for you. It’s a real window, but it’s measured in months, not years — and the drug-coverage window is shorter than the medical one. If retirement is on your calendar, so is this deadline. Call 1-888-808-8282 and we’ll map your dates before they’re behind you.

The late enrollment penalties

Medicare’s deadlines have teeth, and this is the part most people find out about too late.

• Part B: for every full year you could have had Part B but didn’t enroll — and had no coverage that counts — your premium goes up by 10%. That increase is permanent. You don’t pay it once; you pay it every month, for the rest of your life.
• Part D: going without drug coverage adds a smaller monthly penalty that also stays with you for as long as you have a drug plan.

And if you miss your window entirely, you can’t just sign up the next day — you wait for a general enrollment window, and coverage doesn’t start the moment you enroll. Months can go by without coverage.

For later: the Annual Enrollment Period

Every fall (October 15 – December 7), people who are already on Medicare can change plans for the following year. That’s not your concern yet — it becomes relevant once you’re enrolled. File it away for later.