When to Sign Up for Medicare

Medicare has a deadline that does not wait for you to be ready.

Our Medicare page goes further, including how Medicare premiums connect to your tax return from two years earlier.

The seven-month window

Your Initial Enrollment Period runs for seven months: the three months before the month you turn 65, the month itself, and the three months after. Medicare publishes the start date for each month you might sign up in, and coverage always begins on the first of a month.

Write down the month the window opens. Signing up in the earlier part of the window rather than the later part avoids a gap between one coverage ending and the next beginning.

What missing it costs

Two penalties can attach if you miss the window without other qualifying coverage. The Part B penalty is based on how long you could have signed up and did not. The Part D penalty is based on the months you spent without creditable drug coverage, meaning coverage at least as good as Part D, and it applies once you have gone 63 days or more without it.

Both are added to your monthly premium rather than charged once, both grow the longer you wait, and for most people both last as long as you hold that coverage.

If you are still working at 65

Medicare generally gives you a Special Enrollment Period if you or your spouse is still working for the employer that provides your coverage, and the employer is large enough. It runs for eight months after the job or the coverage ends, whichever comes first, and signing up inside it avoids the Part B late enrollment penalty.

Two things to do rather than assume:

• Ask your employer, in writing, to confirm that the plan’s drug coverage is creditable, and keep the letter. It is the evidence that protects you from the Part D penalty.
• Check whether your situation qualifies before you decide to wait. The rules turn on the size of the employer and on whose job the coverage comes from, and getting that wrong is the expensive version of this decision.

The choice that is harder to undo

Once you have Part A and Part B, you choose how to receive your coverage. Original Medicare works with any provider in the country that accepts Medicare, and you can add a separate drug plan and a Medigap supplement. A Medicare Advantage plan comes from a private company approved by Medicare, usually with drug coverage included, often with extras like vision and dental, and usually with a network and some approvals required.

The better fit depends on how you use health care, whether you travel, and what you want your monthly cost to look like.

The way back makes it more than an annual preference. Federal law gives you one Medigap open enrollment period of six months, beginning the first month you are 65 or older and enrolled in Part B. During that window an insurer cannot refuse to sell you a policy or charge you more because of your health. Afterward, in most states, it can do both. So moving from a Medicare Advantage plan to Original Medicare with a supplement several years later may mean answering health questions, and the answers may not go your way.

The choice deserves an afternoon rather than a phone call.

Get impartial help, and then plan around it

Florida SHINE, run by the state Department of Elder Affairs, offers free, unbiased and confidential counseling on Medicare to Florida residents and their families. It is not connected to any insurer or plan.

We add the part SHINE does not do: fitting Medicare into the rest of the plan. That means the calendar, the years before 65 if you are retiring early, and the income decisions in your early sixties that set what you will pay later. If that is the conversation you want, get in touch.