Your Income Decisions Today Set Your Medicare Costs Two Years From Now
Medicare looks back two years at your tax return. One high-income year can increase your premiums by thousands — and most people don't see it coming.
IRMAA: The Medicare Surcharge Nobody Tells You About
IRMAA — Income-Related Monthly Adjustment Amount — is a surcharge added to your Medicare Part B and Part D premiums when your modified adjusted gross income exceeds certain thresholds. It's based on your tax return from two years prior.
2025 IRMAA Thresholds (Based on 2023 Tax Return)
| Filing Status | Income Threshold | Monthly Part B Premium |
|---|---|---|
| Single or MFS | $106,000 or less | $185.00 (standard) |
| Single | $106,001 – $133,500 | $259.00 |
| Single | $133,501 – $167,000 | $370.00 |
| Single | $167,001 – $200,000 | $480.90 |
| Single | $200,001 – $500,000 | $591.90 |
| Single | Above $500,000 | $628.90 |
Source: Centers for Medicare & Medicaid Services. Married filing jointly thresholds are approximately double. These amounts are per person — a couple can pay double.
Hover or tap to see how we address each one.
Roth Conversions & IRMAA
A large IRA-to-Roth conversion can push your income above Medicare surcharge thresholds — costing thousands in higher premiums two years later.
Our Strategy
- Size conversions to stay under Medicare surcharge thresholds
- Project your income 2 years ahead
- Fill lower tax brackets without crossing the line
- Coordinate with required withdrawals and Social Security
Life-Changing Events
Medicare allows IRMAA appeals for retirement, divorce, death of a spouse, or work stoppage. Most people don't know.
Our Strategy
- Help you file Form SSA-44 for qualifying events
- Use a more recent (lower) income year
- Document the life event with proper evidence
- Time the appeal for maximum impact
Capital Gains Planning
Selling a home, business, or investment can trigger a one-time IRMAA spike two years later.
Our Strategy
- Time asset sales around IRMAA windows
- Spread gains across tax years when possible
- Offset gains with losses (tax-loss harvesting)
- Coordinate with Roth conversions in the same year
Enrollment Timing
Part A, B, D, Medigap, Medicare Advantage — when you enroll has permanent consequences. Late penalties never go away.
Our Strategy
- Map your Initial Enrollment Period timeline
- Evaluate Medigap vs. Advantage for your situation
- Coordinate HSA timing with Medicare start date
- Avoid permanent late-enrollment penalties
The Two-Year Lookback in Action
You do a $120K Roth conversion
Nothing happens yet
Medicare sees the $120K — IRMAA kicks in

"IRMAA isn't a penalty — it's a reminder that taxes affect more than just April 15th."
— Rich Ison, Fiduciary Advisor
Medicare Terms That Affect Your Bottom Line
Part A vs Part B
Hospital insurance vs medical insurance — each has different costs and enrollment rules.
Part A vs Part B
Part A covers inpatient hospital stays, skilled nursing (up to 100 days), and hospice. Most people pay $0 in premiums. Part B covers doctor visits, outpatient care, and preventive services — with a standard premium of $185/month in 2025, subject to IRMAA surcharges based on income.
Medigap vs Advantage
Two fundamentally different ways to structure your Medicare coverage after age 65.
Medigap vs Advantage
Medigap supplements Original Medicare — you can see any provider nationwide, with predictable out-of-pocket costs. Medicare Advantage replaces Original Medicare with a private plan — often lower premiums but restricted networks and prior authorizations. Switching back to Medigap later may require medical underwriting.
The IRMAA Lookback
Medicare uses your tax return from two years ago to set this year's premiums.
The IRMAA Lookback
Your 2025 Medicare premiums are based on your 2023 MAGI. A Roth conversion, home sale, or large RMD in 2023 can trigger IRMAA surcharges of $74 to $443 per month per person on top of standard Part B premiums. Planning income two years ahead is essential.
HSA Coordination
You cannot contribute to an HSA once enrolled in any part of Medicare.
HSA Coordination
If you're still working past 65, enrolling in Medicare Part A (even retroactively) ends your HSA contribution eligibility. Since Part A enrollment can be backdated up to 6 months, this can create unexpected tax penalties. Plan the transition carefully with your advisor.

Medicare costs aren't fixed. They're a function of every income decision you make.
Medicare Enrollment Timeline
A month-by-month guide to Medicare enrollment from age 64 to 66 — enrollment windows, penalty deadlines, and the decisions that can't be undone.
- Initial Enrollment Period timeline
- Late penalty calculations
- Medigap vs. Advantage decision tree
- IRMAA income thresholds
- HSA coordination rules
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Medicare Doesn't Exist in a Vacuum
Tax Strategy
IRMAA is a tax planning problem. See how Roth conversion sizing, income timing, and bracket management directly control your Medicare costs.
Retirement Planning
Medicare fits into your broader retirement income plan. See how all the income sources — Social Security, RMDs, investments — interact.
Long-Term Care
Medicare doesn't cover long-term care. Understand the gap and what you need to plan for.

“The decisions you make at 65 about Medicare enrollment follow you for the rest of your life. Late penalties never expire.”
Medicare Planning Questions
Answers to the questions we hear most from Tampa Bay retirees approaching Medicare enrollment.
Medicare Planning Across the Tampa Bay Region
Medicare enrollment decisions are permanent. Missing enrollment windows creates lifetime premium penalties, and income decisions made years earlier can trigger IRMAA surcharges that increase your costs significantly. We help clients throughout the Tampa Bay region coordinate Medicare enrollment with Roth conversions, Social Security timing, and income planning to minimize total costs over a 20-year retirement.
Serving clients in Pasco County, Hillsborough County, Pinellas County, and surrounding areas — including Wesley Chapel, Land O' Lakes, New Tampa, Lutz, Trinity, Odessa, Tampa, St. Petersburg, Clearwater, Brandon, Riverview, Lakeland, and Sarasota. We also work with clients across Florida and those relocating to the state.
Don't Let Your Tax Return Decide Your Medicare Costs
We'll review your income plan alongside your Medicare timeline — so you can make informed decisions before the lookback window locks in.
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