Retirement Insurance Checklist: What to Review Before You Retire

Retiring changes more than your paycheck. Several kinds of insurance may have come through your job, and each one either ends, changes or keeps going on its own terms. This checklist walks through them in the order that usually matters most: health coverage first, then prescriptions, then the gaps Medicare leaves, then the coverage that protects the people you leave behind.

It is a starting list, not advice for your situation. Use it to gather facts, then take each question to the person who can actually answer it.

What should you check first when you plan to retire?

Check your health coverage first. Health insurance and Medicare have the deadlines that can cost you money if you miss them, and the answers shape everything else on the list.

If you are turning 65 around the time you retire. Your Initial Enrollment Period is a seven-month window that starts three months before the month you turn 65. Signing up late for Part B or Part D can mean a penalty that lasts as long as you have that coverage. The turning 65 checklist lays out the months in order.

If you plan to keep working past 65. You may be able to wait on Part B if you or your spouse still have health coverage from current work. Whether waiting makes sense depends on the size of the employer and on the coverage itself, so read how working past 65 works before you skip anything.

If you are retiring before 65. You need a bridge until Medicare starts. The usual options are COBRA, a Marketplace plan or a spouse's employer plan. COBRA generally lets you keep your employer's plan for a limited time, but you typically pay the whole premium yourself. The early retirement guide and the Marketplace and COBRA comparison go through the tradeoffs.

What to ask HR before your last day

How do your prescriptions change the health insurance decision?

They often decide it. Before you compare premiums, write down every medication you take, with the dose and how often you take it.

Every drug plan and Medicare Advantage plan with drug coverage has its own list of covered drugs, and it sorts those drugs into cost tiers. The same medication can sit on different tiers with different companies. One expensive prescription can make a plan with a low premium the costly choice by the end of the year.

Your doctors and hospitals come next. If you are considering a plan with a network, check each provider by name. If you are already on Medicare, the Annual Enrollment Period runs October 15 to December 7, 2026 for 2027 plans, and the Medicare review checklist lists exactly what to bring.

Which costs does Medicare leave for you to plan around?

Original Medicare leaves you deductibles and coinsurance, and it skips several services you may be used to having covered at work.

• Most dental care, routine eye exams, eyeglasses and hearing aids.
• Long-term custodial care, meaning help with daily activities like bathing or dressing, when that is the only care you need.
• A yearly cap on your share of costs. Original Medicare has no out-of-pocket limit by itself. Medicare Advantage plans have a yearly out-of-pocket limit for covered Part A and Part B services. Part D drug costs have separate rules. A Medicare Supplement can cover some or much of Original Medicare cost sharing, depending on the policy.

The full list is in what Medicare doesn't cover. How you fill the gaps is a real tradeoff between premiums now and costs later, which the Medicare Supplement vs Medicare Advantage comparison walks through.

Long-term care deserves its own conversation. The federal LongTermCare.gov site from the Administration for Community Living explains how much care people tend to need and how it gets paid for. Read how Medicare treats skilled and custodial care first, and ask any agent which long-term care options they are actually able to offer before you assume a product fits.

What should you check on life insurance when you retire?

Check what you have, what ends when you leave work, and whether anyone still depends on the money a policy would pay.

The NAIC's buyer's guide suggests a few questions worth answering honestly:

1. Does anyone depend on me financially?
2. How would my family pay my final expenses and any debts?
3. Do I want to leave money to family or a charity?
4. If I have life insurance through my employer, is it enough, and can I keep it?

Retirement often shrinks some needs, like replacing a paycheck, and leaves others, like a spouse who would lose part of a pension or Social Security income. The NAIC also cautions not to cancel a policy you own until a new one is in place, because a change in your health can affect what you qualify for and what you pay.

For the buying side, see life insurance for retirees, term vs whole life and final expense insurance. Review your beneficiaries at the same time, on every policy and account.

Which questions belong with your tax, financial or legal professional?

Anything about taxes, investments, retirement account withdrawals, wills or trusts. An insurance agent can explain how a policy works, but not how it fits your tax return or your estate plan.

Bring these to the right person:

• Retirement income and taxes. How withdrawals and other income will be taxed. Income also matters for Medicare: higher earners pay extra for Part B and Part D, based on the tax return from two years earlier. See how IRMAA works.
• Beneficiary designations. Retirement accounts and life insurance policies each have their own beneficiary forms. Review them with your attorney and the insurer or account custodian so they reflect your intentions and work with your estate plan. Do not assume a change to your will updates a beneficiary form.
• Wills, trusts and powers of attorney. These are legal documents. An attorney drafts them.

How do you put this checklist to work?

Work through it in order, one piece at a time.

1. Gather your papers. Your employer benefits summary, any policies you own, your Medicare card if you have one, a medication list with doses, a list of doctors and a rough monthly budget.
2. Write an end date next to each coverage. Anything that ends when you leave work needs a replacement plan or a deliberate decision to let it go.
3. Settle health coverage first. That means Medicare timing or a bridge plan, checked against your prescriptions and doctors.
4. Then look at life insurance and final bills. Decide what each policy is for and whether you still need it.
5. Send the tax, investment and legal questions to those professionals, with this list in hand.
6. Put next fall on the calendar. Medicare plans change every year, so a yearly review keeps a good choice from going stale.

For unbiased Medicare help, you can use Medicare.gov, call 1-800-MEDICARE (1-800-633-4227, available 24 hours a day, 7 days a week; TTY 1-877-486-2048), or contact Nebraska SHIP at 1-800-234-7119. If you want a licensed agent to go through the insurance pieces with you, call Bill.