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Medicare Cost & Enrollment Planner

Two things blindside higher-income retirees on Medicare: the IRMAA surcharge that quietly raises premiums for life, and the enrollment-window penalties that compound for as long as you’re enrolled. This tool maps both against your specific dates and income.

Medicare looks deceptively simple — Part A is free, Part B has a standard premium — until you’re a higher-income household. Then two things change the math. First, the Income-Related Monthly Adjustment Amount (IRMAA) adds a surcharge to Part B and Part D when your income crosses one of five tier lines, and it’s charged per spouse, every month, for life. Second, if you miss your enrollment window, the late-enrollment penalties are permanent — they don’t expire after a year.

The lifetime cost most people never add up

A married couple paying the standard Part B premium plus a Medigap policy and a Part D plan is looking at real five- and six-figure spending across a 25-year retirement. Layer an IRMAA surcharge on top — even one tier — and you add thousands per year, per spouse. This calculator projects that total so you can see it as one number instead of a line item that creeps up every January.

The enrollment traps

Your Initial Enrollment Period runs the three months before, the month of, and the three months after your 65th birthday. Miss it without qualifying coverage and the Part B penalty is 10% for every full 12 months you were eligible but not enrolled — added to your premium permanently. The most common trap: assuming COBRA counts as active employer coverage. It doesn’t. If you’re working past 65, your Special Enrollment Period runs only eight months after your active employment ends — COBRA does not extend it.

There’s also a one-time Medigap window: a six-month Open Enrollment Period beginning when your Part B starts, during which insurers can’t deny you or price you up for health history. Once it closes, that protection is gone in most states.

What this calculator does

Enter your filing status, birth month and year, current income, and a few coverage assumptions. The tool will show you:

  • Your IRMAA tier and the monthly Part B + Part D surcharge it carries
  • Your estimated monthly and annual household Medicare cost
  • A lifetime projection to your chosen longevity age
  • Your enrollment windows — IEP, Medigap OEP, and (if you’re working past 65) your Special Enrollment Period — with any penalty exposure flagged

Coordinating Medicare costs with Roth conversion timing, Social Security claiming, and your withdrawal sequence is exactly the kind of financial advice we provide at T&T Capital Management for households with $500K+ in investable assets. This calculator is the clear-eyed starting point.

Run yours.

Coverage roadPremiums below are your estimates
Math runs in ~1 second. We don’t store your inputs.

How this works: Costs use the 2026 standard Part B premium and the CMS IRMAA tables; your tier is set by your modified adjusted gross income from two years prior. Medigap, Part D, and Medicare Advantage premiums are your estimates — actual premiums vary by plan, state, and health. The lifetime projection is in today’s dollars and does not adjust for inflation or future premium increases. Penalty figures are estimates based on the dates you enter.

Not affiliated with the government. T&T Capital Management is not connected with or endorsed by the U.S. government, Medicare, or CMS, and we are not a licensed insurance agent or broker. We do not sell, name, rank, or recommend any specific Medigap, Medicare Advantage, or Part D plan. This tool provides general financial advice on the cost and timing of Medicare; it is illustrative and is not insurance or enrollment advice. Verify all figures and enrollment dates at medicare.gov.

T&T Capital Management is an SEC-registered investment adviser. To talk with us about your specific situation, schedule a free consultation.