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Turning 65? The Medicare Enrollment Deadlines That Carry Lifetime Penalties

An hourglass against a textured gray wall, with a sticky note reading “For life?”.
Photo by Alexandar Todov on Unsplash

If you aren't already collecting Social Security when you turn 65, nobody signs you up for Medicare. You do it yourself, and you get seven months. Let them pass without the right kind of other coverage, and a surcharge lands on your Part B premium: 10% for every full 12 months you went without. It stays for as long as you have Part B. People who pay it usually made one assumption that sounded sensible.

See who can safely delay Part B

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By Margaret Linwood · Updated Sep 29, 2026 · Reviewed against Medicare.gov, SSA, CMS

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The assumptions are easy to make. COBRA feels like the same coverage you had at work. A retiree plan from a former employer seems like reason enough to wait. And if you don't take a single prescription, why pay for drug coverage? Medicare accepts none of them.

Money isn't all you lose, either. Say the window slips by and there's no special enrollment right to fall back on. Then you wait for the General Enrollment Period, January 1 through March 31, and Part B won't start until the month after you sign up. So what if you notice in April? You could go most of a year with no Part B at all.

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Where your seven months actually fall

It sounds more complicated than it is. The part people don't expect is that your coverage start date moves depending on which month you apply in.

  1. Where it starts and ends. Picture a June 14 birthday. Your window opens March 1, three months before the birthday month, and stays open until September 30, three months after it.
  2. Early beats late. Apply in any of the three months before your birthday month and Part B starts the first day of that month, but wait until later and it starts the first of the month after you apply, so you could be uncovered for a few weeks.
  3. Born on the 1st? Then everything slides a month earlier, and a June 1 birthday gets you February 1 through August 31.
  4. Who gets signed up without asking. Only people who've been on Social Security or Railroad Retirement benefits for at least four months before turning 65. If that's not you, you apply on your own, online through Social Security, by phone or at a local office.
  5. The drug clock runs faster. If you go 63 days or more in a row without Part D or other creditable drug coverage, there's a separate penalty, and you'd pay it for as long as you have Medicare drug coverage.

Getting the dates right is only half of it. The article also walks through a sign-up timeline that starts six months before 65, with the two forms you'll need once job coverage ends.

See the sign-up timeline, step by step

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