Retiring before 65: how to bridge the gap to Medicare
Health insurance is the reason a lot of people work longer than they need to. It is a solvable problem, and the solution is mostly about how you manage income in the bridge years.
If you retire at 62, you have three years to cover before Medicare. For many households that gap is the single biggest obstacle to retiring at all — and it is far more manageable than it looks, provided you plan the income side deliberately.
Your options, honestly assessed
For most people retiring before 65 without a working spouse, the Marketplace is where the answer lives. What makes it work is that your income in retirement is often exactly the kind of income the subsidy structure is designed around.
- A Marketplace plan with an advance premium tax credit — the primary route for most early retirees, and the one where planning pays
- A spouse's employer plan, if one is still working — usually the simplest answer when it is available
- COBRA from your former employer — familiar and unsubsidised, typically capped at 18 months
- Retiree coverage from a former employer, if you are fortunate enough to have it offered
- Short-term medical — a stopgap only, with real exclusions, and not eligible for the tax credit
The insight that changes the maths
The premium tax credit is based on your modified adjusted gross income for the year — not on your net worth, and not on what you have saved. A household with substantial retirement assets can have modest taxable income, and the credit follows the income.
That means how you fund your living expenses in the bridge years directly changes what you pay for health insurance. Which accounts you draw from, when you realise gains, and whether you convert to a Roth before or after 65 are health insurance decisions as well as tax decisions.
What counts as income, and what does not
Broadly, these are counted:
- Taxable withdrawals from traditional IRAs and 401(k)s
- Roth conversions in the year you convert
- Realised capital gains, dividends and taxable interest
- Pension payments and any wages or self-employment income
- The taxable portion of Social Security, plus tax-exempt interest added back
Where the thresholds sit
Two thresholds matter in the bridge years. Below roughly 250% of the federal poverty level for your household size, cost-sharing reductions are available on Silver plans — which materially lowers your deductible and copays, not just your premium.
Above that, credits continue on a sliding scale, so there is no single cliff to fall off, but the amount tapers. The practical point is that a Roth conversion or a large realised gain in a bridge year can quietly cost you thousands in lost credits and lost cost-sharing reductions. That trade may still be worth making — but it should be a decision, not an accident.
Do not forget the rest of the picture
Medicare covers dental, vision and hearing barely or not at all, and neither does a Marketplace plan in the way people assume. If you have dental work you have been postponing until retirement, price standalone coverage before you retire rather than after.
It is also worth thinking about how the bridge ends. The transition to Medicare at 65 has its own deadlines, and your Marketplace plan does not roll into Medicare automatically. Plan that handoff about six months out.
A realistic sequence
- Twelve months before retiring: estimate your bridge-year income under two or three drawdown strategies
- Nine months before: price Marketplace plans in your county at each income level, and check the cost-sharing reduction threshold
- Six months before: check your doctors and prescriptions against the plans you are considering
- Three months before: confirm your Special Enrollment Period timing so coverage starts the day the old plan ends
- Each autumn during the bridge: re-run the numbers, because plans, prices and your income all change
- Six months before 65: start the Medicare conversation and plan the handoff
Coordinate, do not improvise
The health insurance decision and the drawdown decision are the same decision viewed from two angles, and they are usually made by two different people who never speak. Your tax professional owns the tax side. An insurance agent who understands the subsidy structure owns the coverage side.
Getting them to look at the same numbers once, before you retire, is worth more than any single plan choice you will make in those years.
The bottom line
Retiring before 65 is a solvable problem. Plan the income side, check the cost-sharing reduction threshold, and start about a year out. Sarah works with early retirees across Northern Utah on exactly this bridge — and she will tell you plainly if a spouse's plan or COBRA is the better answer.
Want to go through this with someone?
Sarah will go through your doctors, your prescriptions and your real numbers, and tell you plainly what she found. No cost, no pressure.
Please note: CUPS Insurance is not affiliated with, endorsed by, or operating on behalf of HealthCare.gov, the Health Insurance Marketplace, or any federal or state government agency. Plan availability, premiums and advance premium tax credits are set by the carriers and the Marketplace. Estimates only. Figures on this page use published 2026 plan-year values and the details you enter. They are not a quote, an offer of coverage, or a determination of eligibility. Your final premium and any advance premium tax credit are confirmed at enrollment on HealthCare.gov or with the carrier.