Chaperone Health Insurance Plus
Medicare Planning for High-Net-Worth South Floridians: IRMAA, Roth Conversions, and HSAs
Reviewed October 2026 · Covers the 2027 plan year
Most people expect their Medicare premiums to be the same as everyone else’s. Then a letter from Social Security arrives saying they’ll pay more, because of income they reported two years earlier. That extra charge is called IRMAA, and it can follow a Roth conversion, a home or business sale, a large capital gain, or simply growing required distributions from retirement accounts. It can affect people at many income levels, including people whose income was high for only one year.
I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, based in Fort Lauderdale. I’ve spent 14 years in insurance and the last 8 focused on Medicare, and I help my clients understand how Medicare IRMAA shows up in their coverage costs, so they and their tax professionals can plan around it. This guide explains how the IRMAA brackets work, what counts as income, how to ask for a lower amount after a life-changing event, and how HSAs fit in. I can’t give tax or legal advice, so I’ll point out where your CPA or financial advisor should weigh in. When you’re ready, book a free plan review and I’ll get back to you personally within 24 to 48 hours.
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Get a Free Quote From a Medicare Broker Who Plans Around the 2027 IRMAA Brackets
IRMAA doesn’t change which plans you can buy, but it changes what Medicare costs you, so when I review your options, I check:
- Any income-related amount you’re paying, or may pay, as part of each plan’s full-year cost
- Your doctors and hospitals against each plan’s network, including HCA Florida, Memorial, and Baptist Health
- Your prescriptions and pharmacy against each drug list
If anything is unclear, I call your doctor’s office to confirm it, and I’m glad to coordinate with your CPA or financial advisor on the Medicare side. Your quote is free, with no obligation to enroll. Get your free quote and I’ll do the research for you.
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Why Choose Me for IRMAA and Medicare Planning
When your income affects your Medicare premiums, here’s what to look for in an agent, and what you can expect from me.
Working Alongside Your CPA or Financial Advisor: I handle the Medicare side and explain how each bracket changes your premiums. Your tax professional handles the tax planning, and I can’t give tax or legal advice. With your permission, I’m glad to share what I find with them.
Your Doctors, Hospitals, and Prescriptions Checked First: Before I recommend any plan, I check your doctors, hospitals, and every prescription against its network and drug list, including your pharmacy. If something is unclear, I’ll call your doctor’s office myself.
Every Question Answered, at Your Pace: IRMAA, the two-year lookback, and the appeal form are confusing, and most people spend less than an hour on their Medicare choices. I take as long as you need, explain each piece in plain language, and answer every question until it makes sense. There’s no pressure and no obligation to enroll.
The Plan That Costs Less for You: I add any income-related amount to the premium, deductible, copays, and drug costs for each plan we compare, so you see the real yearly total.
My Help Costs You Nothing Extra: Insurers pay my commission, and plan premiums are generally the same whether you enroll through me or directly, so you get personal guidance and ongoing support at no additional charge.
Both Paths, Side by Side: Medicare Advantage, Medigap, and Part D each work differently. I lay out every path that fits your situation and explain what you’d gain and give up with each, so you decide with the full picture.
I Handle the Paperwork and the Timing: If you’re working past 65, I help you plan your Part A and Part B start dates around your employer coverage and your last HSA contribution, so retroactive coverage doesn’t catch you by surprise. If you choose a plan, I complete the application with you and follow it through to approval.
Licensed and Verified: I’m licensed in 33 states, I complete AHIP’s annual Medicare certification, and I’m certified for the 2027 plan year. You can verify my license (Florida License #W323530, NPN #17946070) anytime through your state’s insurance department.
I Stay Your Agent After You Enroll: Work with me directly, in person, by phone, on Zoom, or at your home in Broward, Miami-Dade, or Palm Beach, and I reply within 24 to 48 hours. Your IRMAA bracket and your plan’s costs can both change every year, so I review your coverage every Annual Enrollment Period and reply when a new Social Security letter or bill raises questions.
You can read all 25 reasons we should work together on my Why Choose Me page.
What Is IRMAA?
IRMAA stands for income-related monthly adjustment amount. It’s an extra amount people with higher incomes pay on top of their Medicare Part B premium and their Part D drug coverage premium. Social Security decides whether you owe it, and how much, based on your income. According to the Social Security Administration, people who pay IRMAA cover 35% to 85% of the total cost of Part B coverage, instead of the standard share.
It’s based on your modified adjusted gross income (MAGI): For IRMAA, Social Security defines MAGI as your adjusted gross income plus any tax-exempt interest, such as interest from municipal bonds. Your adjusted gross income is the figure on your federal tax return, so anything that raises it, from wages to investment gains, can raise your MAGI too.
It looks back two years: Social Security uses the most recent tax return the IRS gives it, which is usually from two years before the premium year. For 2026, that’s generally your 2024 return. For 2027, it will generally be your 2025 return. That means a decision you made in 2025 may affect what you pay for Medicare in 2027, even if your income has already gone down.
It’s recalculated every year: IRMAA isn’t permanent. Each year, Social Security looks at a new tax year. If your income drops below the first threshold, the extra amount goes away for that year. If it rises, you may move into a higher bracket.
It’s charged per person: If you and your spouse are both on Medicare and your joint income is over a threshold, each of you pays the income-related amount on your own premiums.
How it’s paid: The Part B and Part D amounts are usually taken out of your Social Security benefit. If you don’t receive Social Security yet, or the amount is more than your benefit, Medicare sends you a bill. CMS says the Part D amount must be paid to Medicare, not to your drug plan, and you need to pay it to keep your Part D coverage.
IRMAA Brackets 2027: Where the Numbers Stand
As of October 27, 2026, CMS has not yet published the 2027 Part B premium or the IRMAA brackets 2027 will use. CMS usually announces them each fall in its Part B premium fact sheet, often in mid-November. I’ll update this guide as soon as the official 2027 figures are released. Until then, be careful with any 2027 numbers you see online: unless they come from CMS or Social Security, they’re estimates.
Here’s how the Medicare IRMAA brackets work today, using the official 2026 figures that CMS published on November 14, 2025. They’re based on your 2024 tax return. The Part B column shows your total monthly Part B premium, including the standard 2026 premium of $202.90. The Part D column shows the amount added to your drug plan’s premium, whatever plan you have.
| 2026 Individual Return (2024 MAGI) | 2026 Joint Return (2024 MAGI) | 2026 Part B Monthly Premium | 2026 Part D Monthly IRMAA |
|---|---|---|---|
| $109,000 or less | $218,000 or less | $202.90 | $0.00 |
| $109,001 to $137,000 | $218,001 to $274,000 | $284.10 | $14.50 |
| $137,001 to $171,000 | $274,001 to $342,000 | $405.80 | $37.50 |
| $171,001 to $205,000 | $342,001 to $410,000 | $527.50 | $60.40 |
| $205,001 to less than $500,000 | $410,001 to less than $750,000 | $649.20 | $83.30 |
| $500,000 or more | $750,000 or more | $689.90 | $91.00 |
Source: CMS, “2026 Medicare Parts A & B Premiums and Deductibles” fact sheet, November 14, 2025. Figures apply to the 2026 plan year only.
If you’re married and file separately but lived with your spouse at any time during the year, CMS uses a separate, shorter chart for 2026: $109,000 or less pays the standard premium, $109,001 to less than $391,000 pays $649.20 a month for Part B plus $83.30 for Part D, and $391,000 or more pays $689.90 for Part B plus $91.00 for Part D.
One detail surprises a lot of people: the brackets work like steps, not a gradual slope. Going even $1 over a threshold moves you into the next bracket’s full amount for that year. That’s why it helps to know where your income is likely to land before a large, one-time transaction, and to talk it through with your tax professional.
How Roth Conversions, Capital Gains, RMDs, and Home or Business Sales Affect IRMAA Medicare Premiums
Because IRMAA follows your MAGI, it can be triggered by income you don’t think of as income. These are the events I see most often with my clients. In each case, the timing and the tax details belong with your CPA or financial advisor, since I can’t give tax or legal advice.
Roth conversions: When you convert money from a traditional IRA or 401(k) to a Roth IRA, the converted amount is generally taxable in the year you convert, so it adds to your adjusted gross income and your MAGI. A large conversion in 2025 may show up on your 2027 Medicare premiums. Later withdrawals from a Roth IRA that meet the IRS rules generally aren’t taxable, which is one reason some people and their advisors consider conversions. Whether that trade-off makes sense for you is a tax question.
Capital gains: Selling stocks, funds, or other investments at a gain adds to your income for that year. So can capital gain distributions from mutual funds, even if you didn’t sell anything.
Home sales: If you sell your main home, current IRS rules (as of 2026) let many people exclude up to $250,000 of gain, or up to $500,000 for married couples filing jointly, if they meet the ownership and use tests. Gain above the exclusion, or gain on a second home or rental property, generally counts as income. Many South Floridians sell a home up north or downsize here, so this one comes up often.
Business sales: Selling a business or business property can create a large gain in a single year, which may push your MAGI into a higher bracket two years later.
Required minimum distributions (RMDs): Under current IRS rules, most people must start taking withdrawals from traditional IRAs and workplace retirement plans at age 73. Those withdrawals are generally taxable, and they can grow over time as you age, so income that was under a threshold in your late 60s may cross it later. Roth IRAs don’t require withdrawals during the original owner’s lifetime.
Other income: Wages, pension income, the taxable part of your Social Security benefits, interest, dividends, and tax-exempt interest can all add to the MAGI Social Security uses.
I don’t recommend how much to convert, when to sell, or how to structure a transaction. What I can do is show you how a higher or lower bracket would change your Medicare costs, so you and your CPA have that number when you plan. If you work with a CPA or financial advisor, they can see how I work alongside professionals on my For Professionals page.
Appealing IRMAA With Form SSA-44 After a Life-Changing Event
If your income has gone down since the tax year Social Security used, you may be able to ask for a new decision based on more recent income. You do this with Form SSA-44, “Medicare Income-Related Monthly Adjustment Amount, Life-Changing Event.” Based on the current form (revision 12-2025), these are the events Social Security accepts:
Marriage: you entered into a legal marriage.
Divorce or annulment: your marriage ended, and you won’t file a joint return with your former spouse for that year.
Death of your spouse.
Work stoppage or reduction: you or your spouse stopped working or cut back your hours. Retirement is the most common example.
Loss of income-producing property: you or your spouse lost property that produced income, through no sale or transfer of your own, such as a loss in a declared disaster area, arson, or investment fraud or theft.
Loss of pension income: a scheduled end, termination, or reorganization of an employer’s pension plan reduced your or your spouse’s pension.
Employer settlement payment: you or your spouse received a settlement from an employer or former employer because of that employer’s bankruptcy or reorganization.
You’ll need documents that prove the event, such as a signed employer statement or pay stubs for a work stoppage, and proof of your income, such as a signed tax return or IRS transcript. If you send an estimate of your income for the current year, Social Security asks you to send a copy of your filed return later. You can submit Form SSA-44 online through your my Social Security account, by mail or fax to a Social Security office, or by calling Social Security at 1-800-772-1213 (TTY 1-800-325-0778).
It’s just as important to know what isn’t on the list. A Roth conversion, a home sale, or a one-time capital gain isn’t a life-changing event on Form SSA-44, so income from those generally can’t be removed this way. If you think Social Security used the wrong tax information, or you filed an amended return, that’s a different process: Social Security says to send a copy of the amended return and the IRS acknowledgment, or to correct wrong income information with the IRS. If you disagree with the decision for another reason, you can ask for reconsideration with Form SSA-561-U2. Your CPA can help you decide which route fits.
HSAs and Medicare: When to Stop Contributing
If you’re working past 65 and contributing to a Health Savings Account, Medicare timing matters. Once you’re enrolled in any part of Medicare, including Part A, your HSA contribution limit drops to zero for that month and every month after, according to IRS Publication 969.
The part that catches people off guard is retroactive coverage. If you sign up for Part A after you turn 65, or apply for Social Security retirement benefits, which enrolls you in Part A automatically, Medicare says your Part A coverage generally starts up to six months back from the month you sign up, though not earlier than the month you turned 65. Contributions made during those backdated months may count as excess contributions, and the IRS generally charges a 6% excise tax on excess contributions for each year they stay in the account.
That’s why Medicare.gov advises that you and your employer stop contributing to your HSA six months before you retire or apply for Social Security benefits. If you’re not sure when your Medicare will start, talk with your HR department and your tax professional before you set your final contribution.
You can still use money already in your HSA after you enroll in Medicare. IRS Publication 969 lists Medicare coverage for people 65 or older as a qualified expense, which can include Part B, Part D, and Medicare Advantage premiums, but not Medigap premiums. The details depend on your situation, so check them with your CPA. I help people turning 65 or retiring plan their Medicare start date, and my Turning 65 Medicare Checklist walks through the rest of the timeline.
How IRMAA Affects Your Medicare Plan Choice
IRMAA follows you no matter which Medicare path you choose. It isn’t something a plan can waive, and switching plans won’t remove it. Here’s how it applies to each path:
Original Medicare with Medigap and Part D: you pay the Part B premium plus any Part B IRMAA, your Medigap premium (Medigap premiums aren’t income-adjusted by Medicare), and your Part D plan premium plus any Part D IRMAA. My Medigap cost guide explains what sets Medigap premiums in Florida.
Medicare Advantage: you still pay your Part B premium, including any Part B IRMAA, to stay in the plan. If the plan includes drug coverage, the Part D IRMAA applies too. CMS says this is true even when your drug coverage comes through an employer or union plan.
Standalone Part D: the Part D IRMAA is the same dollar amount for everyone in your bracket, whichever drug plan you choose, because it’s based on a national figure, not your plan’s premium. My guide to 2027 Medicare Part D costs covers the deductible, drug stages, and out-of-pocket limit.
Because IRMAA is the same across plans in a given path, it shouldn’t be the main reason to choose one plan over another. The bigger questions are still your doctors, your hospitals, your prescriptions, how often you travel or spend time out of state, and how much cost sharing you’re comfortable with. Each path has trade-offs: Medicare Advantage plans usually use networks and have an out-of-pocket maximum, while Medigap plans generally let you see any provider who accepts Medicare but come with a separate premium and usually need a separate Part D plan. Including IRMAA in the full-year comparison simply makes the total more accurate.
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Frequently Asked Questions About IRMAA and Medicare Planning
How Do the IRMAA Brackets 2026 Compare With 2027?
For 2026, IRMAA starts at MAGI above $109,000 for individual returns and above $218,000 for joint returns, based on 2024 tax returns, and the standard 2026 Part B premium is $202.90 a month. As of October 27, 2026, CMS hasn’t published the 2027 figures yet. When it does, the 2027 brackets will generally be based on 2025 tax returns. The lower thresholds are usually adjusted for inflation each year, so the 2027 starting points may be somewhat higher than 2026’s, but the official numbers are the only ones to rely on. I’ll update this guide when they’re released.
When Will the 2027 IRMAA Brackets Be Released?
CMS usually announces the next year’s Part B premium and IRMAA brackets in the fall, often in mid-November. Social Security then mails IRMAA notices to people who owe an income-related amount. If you get a notice for 2027, read it carefully, since it shows the tax year and income Social Security used.
Does Medicare IRMAA Apply if I Have a Medicare Advantage Plan?
Yes. Medicare Advantage members still pay their Part B premium, including any Part B IRMAA. If your Medicare Advantage plan includes drug coverage, the Part D IRMAA applies too, and CMS says the same is true for drug coverage through an employer plan.
Can a Roth Conversion Raise My Medicare Premiums?
It can. The converted amount is generally taxable income in the year you convert, so it adds to your MAGI. Because of the two-year lookback, a 2025 conversion may affect your 2027 premiums. A Roth conversion isn’t a life-changing event on Form SSA-44, so the higher amount generally can’t be appealed on that basis. Talk with your CPA or financial advisor before converting, since I can’t give tax advice.
Can You Tell Me How Much to Convert or How to Lower My Taxes?
No. I’m a licensed insurance agent, and I can’t give tax or legal advice. What I can do is show you how each IRMAA bracket would change your Medicare costs, so your CPA or financial advisor can include that in your plan. If your advisor would like to work with me, they can learn more on my For Professionals page.
What if I Retired and My Income Dropped?
Retirement can count as a work stoppage, one of the life-changing events on Form SSA-44. If your income has gone down since the tax year Social Security used, you can ask for a new decision with Form SSA-44 and proof of the event and your income. Social Security decides whether the request qualifies.
Will I Pay IRMAA Every Year?
Not necessarily. Social Security recalculates it every year using a newer tax return. If your MAGI falls below the first threshold for that year, you pay the standard premium. If it rises, you may move into a higher bracket.
Where Can I Learn More About My Medicare Options?
My Medicare Knowledge Center has guides on enrollment timing, plan comparisons, and costs. For questions about your IRMAA decision, you can call Social Security at 1-800-772-1213 (TTY 1-800-325-0778).
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Have a Social Security IRMAA letter or a big income year coming up? Pick a time for a free 15-minute call by phone or video, and I’ll show you how it affects your Medicare costs. My help never costs you anything extra.
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