Planning
What to do in the six months before you turn 65
Almost everything that goes wrong at 65 goes wrong because of timing. Here is the order to do things in, month by month, starting half a year out.
If you only do three things
- Stop HSA contributions now, six months out.
- Ask HR, in writing, whether your plan stays primary after 65.
- Put the first day of your enrollment window in your calendar with an alarm.
Six months out
Stop contributing to your HSA
This is the single most common expensive mistake, and it has to happen now rather than later. When you eventually enroll in Medicare, Part A can back-date coverage up to six months. Any HSA contribution made during a month Medicare retroactively covers is an excess contribution, and the IRS taxes it. Money already in the account is fine — you can spend it on qualified expenses forever. It's new deposits that have to stop.
Get your employer's answer in writing
Ask HR two specific questions: does the company have 20 or more employees, and does the plan remain the primary payer once I turn 65? If the answer to either is no, Medicare becomes primary and delaying Part B can leave you with almost no coverage. Keep the reply — if you later need a Special Enrollment Period, Social Security will ask your employer to confirm it anyway.
Pull your Social Security estimate
Create a my Social Security account at SSA.gov and look at your benefit at 62, at full retirement age, and at 70. Check your earnings record while you're there — errors are more common than you'd expect and take time to correct. You don't have to decide anything yet. You just need the numbers in front of you.
Four months out
Choose your Medicare path
There are two routes and you should pick before your window opens, not during it. Original Medicare plus a Medigap policy plus a Part D drug plan gives you any doctor who accepts Medicare, predictable costs, and no referrals — for a higher monthly premium. Medicare Advantage bundles everything, often adds dental and vision, and costs less monthly — but you stay inside a network and pay more when you use care. If you travel often or split the year between two states, that network matters more than the premium.
Write down your prescriptions and your doctors
Every drug, dose, and pharmacy; every doctor you want to keep. Part D plans cover different drug lists and Advantage plans cover different doctors, so this list is what you compare plans against. Medicare's own Plan Finder accepts it directly and will price your actual year, not an average one.
Refresh your estate documents
A will or living trust, a durable financial power of attorney, a healthcare power of attorney, and an advance directive. Then check the beneficiary designations on every retirement account and insurance policy — those override your will, and an ex-spouse left on a form from 1998 will inherit exactly as written.
Three months out — your window opens
This is the month that matters. Enrolling now, in one of the three months before your birthday month, is what makes coverage start on the first day of your birthday month with no gap. Wait until your birthday month and coverage slips by a month.
Apply for Parts A and B at SSA.gov
About fifteen minutes online. If you're already collecting Social Security, skip this — you were enrolled automatically and your card is already in the post.
Apply for Medigap in the same stretch
Your Medigap open enrollment is a single six-month period beginning when Part B starts. During it, no insurer can refuse you or charge more because of your health. Afterwards, in most states, they can do both. If you want Medigap, this is effectively your only guaranteed chance at it.
Decide about Social Security separately
Medicare at 65 does not mean Social Security at 65. They are separate decisions with separate deadlines, and for most people claiming at 65 means a permanently reduced benefit. Delaying past full retirement age adds roughly 8% a year up to 70. Decide it on its own merits.
The month itself
Check that your Medicare card arrived and that the effective date on it is what you expected. Book your Welcome to Medicare visit — it’s free during your first twelve months on Part B and it never comes back. Tell your doctors’ offices and your pharmacy your new coverage details before the first appointment, not at it.
Then set one more reminder: 15 October, every year. Open Enrollment runs to 7 December and plans change their drug lists and networks annually. The plan that was right this year is not automatically right next year.
Sources
- Medicare.gov — enrollment periods, Medigap open enrollment, preventive visits
- SSA.gov — benefit estimates and full retirement age
- IRS Publication 969 — HSA contributions and Medicare
This is information, not advice. Your dates and coverage rules depend on your own circumstances. Confirm anything decision-critical with Medicare, Social Security, or a licensed advisor. Suddenly65 is not connected with or endorsed by the U.S. government or the federal Medicare program.
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