What a Roth Conversion Changes About the Check — and What It Doesn't

Your Social Security Has a Gross and a Net

Most people file Roth conversions under taxes. The same move changes how much of a Social Security benefit is taxable, what Medicare withholds from the check, and what a surviving spouse keeps. A worked example, year by year.

Mark Annese
Mark AnneseCo-Founder of IRMAA Certified Planner, Founder of RetirementAdvisorProAugust 21, 2026Updated August 21, 20269 min read

The pushback was fair: “this just changes when I pay taxes”

A conversation with an advisor last week, about a client stuck on a Roth conversion. The client's objection was the standard one, and it is not wrong on its face: a conversion moves a tax bill from the future into the present. If the rates are similar, why bother?

Here is the framing that landed.

Your Social Security has a gross and a net — just like a paycheck. The award letter states a gross figure. What reaches the bank account is smaller, because Medicare premiums and income-based surcharges are deducted from the benefit before it is paid — that is federal law, not a plan choice. And what the retiree keeps is smaller still, because up to 85% of the gross benefit is taxable.

A Roth conversion is one of the few moves that changes the net without touching the gross. In the scenario modeled below, both paths — convert and don't convert — pay the client the identical $1,575,798 of gross Social Security over 26 years. The conversion path delivers $193,305 more of it.

Same benefit. Bigger deposit. Three mechanisms do the work, and they compound in that order.

Leak one: how much of the benefit is taxable

The IRS decides how much of a benefit is taxable with a formula: one-half of benefits, plus all other income — including tax-exempt interest. Traditional IRA withdrawals are ordinary income inside that formula. Qualified Roth withdrawals are excluded from gross income entirely, so they never enter it.

Every dollar sitting in a traditional account is a dollar that will eventually feed that formula, because required minimum distributions force it out. Every converted dollar stops feeding it, forever.

Taxable benefit without conversionTaxable benefit with conversion
$50k$25kAge 75, without conversion: $48,492 taxableAge 75, with conversion: $31,984 taxable75Age 76, without conversion: $49,461 taxableAge 76, with conversion: $34,573 taxable76Age 77, without conversion: $50,451 taxableAge 77, with conversion: $37,145 taxable77Age 78, without conversion: $51,460 taxableAge 78, with conversion: $40,015 taxable78Age 79, without conversion: $52,489 taxableAge 79, with conversion: $43,041 taxable79Age 80, without conversion: $53,539 taxableAge 80, with conversion: $46,232 taxable80Age 81, without conversion: $54,609 taxableAge 81, with conversion: $49,353 taxable81Age 82, without conversion: $55,702 taxableAge 82, with conversion: $52,882 taxable82Age 83, without conversion: $56,816 taxableAge 83, with conversion: $56,302 taxable83
Amount of the Social Security benefit that is taxable each year, ages 75–83 — the window between RMD start and the year both paths hit the 85% maximum. Without the conversion, required distributions push the benefit to its maximum taxable share immediately at 75. With the conversion, up to $16,508 less of the benefit is taxable in a single year. From 84 on, both paths sit at the 85% cap and the difference closes. Modeled in RetirementAdvisorPro; single filer.

In the modeled scenario the difference shows up exactly where the mechanism predicts: the year required distributions begin. At 75, the client who didn't convert has $48,492 of the benefit taxable — the 85% maximum, immediately. The client who converted has $31,984 taxable — $16,508 less, in one year. The gap persists for nine years before rising income pins both paths at the cap.

Two honest boundaries on this claim. High-income retirees sit at the 85% maximum with or without a conversion — for them this first leak barely moves. And taxes on benefits are normally paid at filing, not withheld from the check, so this leak reduces what the retiree keeps, not the deposit itself. The deposit is the next mechanism's job.

Leak two: what Medicare takes out of the check

Medicare Part B premiums are collected, by statute, "by deducting the amount thereof" from the monthly benefit. The income-based surcharges — IRMAA — ride the same rail. They never arrive as a bill; the check simply shrinks.

And IRMAA runs on modified adjusted gross income from two years prior. That delay is why almost nobody connects the surcharge back to its cause.

Surcharge without conversionSurcharge with conversion
$30k$20k$10kAge 70, without conversion: $0Age 70, with conversion: $070Age 71, without conversion: $0Age 71, with conversion: $0Age 72, without conversion: $0Age 72, with conversion: $0Age 73, without conversion: $0Age 73, with conversion: $0Age 74, without conversion: $0Age 74, with conversion: $0Age 75, without conversion: $0Age 75, with conversion: $075Age 76, without conversion: $0Age 76, with conversion: $0Age 77, without conversion: $3,450Age 77, with conversion: $0Age 78, without conversion: $3,697Age 78, with conversion: $0Age 79, without conversion: $3,960Age 79, with conversion: $0Age 80, without conversion: $4,243Age 80, with conversion: $080Age 81, without conversion: $11,408Age 81, with conversion: $0Age 82, without conversion: $12,222Age 82, with conversion: $0Age 83, without conversion: $13,094Age 83, with conversion: $0Age 84, without conversion: $14,029Age 84, with conversion: $0Age 85, without conversion: $15,031Age 85, with conversion: $085Age 86, without conversion: $16,104Age 86, with conversion: $0Age 87, without conversion: $27,626Age 87, with conversion: $0Age 88, without conversion: $29,600Age 88, with conversion: $7,369Age 89, without conversion: $31,716Age 89, with conversion: $7,896Age 90, without conversion: $33,983Age 90, with conversion: $8,46190RMDs begin (75)surcharge lands (77)$33,983With conversion: $0 until 88
Annual income-based Medicare surcharges (IRMAA) withheld from the Social Security benefit, ages 70–90, modeled in RetirementAdvisorPro. Without the conversion, required distributions begin at 75 and the surcharge lands at 77 — two years later, because IRMAA runs on income from two years prior. With the $500,000 conversion done at 61, the account that generates those distributions is a fraction of the size, and the surcharge stays at zero until 88. Assumes Part B premiums grow 7.3%/yr and Part D 6%/yr; single filer.

Watch the two-year lookback do its work. Without the conversion, required distributions begin at 75 — and the surcharge lands at 77, starting at $3,450 and climbing the tiers to $33,983 a year by 90 as distributions compound. Lifetime surcharges: $220,162.

The conversion path faces the same rules with a different input. The $500,000 conversion at 61 cut the traditional account that generates those distributions — lifetime RMDs fall from $2.37 million to $980,000 — so the income that sets the surcharge stays under the thresholds until 88. Lifetime surcharges: $26,857.

One precision point worth getting right in client conversations: the conversion does not touch the standard Part B premium — everyone pays that. It only removes the income-based surcharge stacked on top. In this scenario that stack was worth $193,305.

Leak three: what the surviving spouse keeps

The modeled client is single, so this scenario cannot show the third leak — but for couples it is the sharpest one. When one spouse dies, the survivor keeps roughly the larger Social Security benefit and most of the household income, then files single: about half the bracket room, and IRMAA thresholds at half the married level. Every mechanism above gets meaner at exactly the moment one person is left depending on the check.

We've published the year-by-year math on that separately — the same retirement that costs $82,352 in surcharges as a couple costs $342,386 for the widow. A conversion executed while both spouses are alive — at married-filing-jointly brackets and married IRMAA thresholds — is the one version of this move the survivor cannot make alone later.

The whole picture — and the year this runs in reverse

Standard premiums (identical in both paths)Income-based surcharges (IRMAA)
Standard premiums: $306,368Surcharges without conversion: $220,162$526,530Without conversionStandard premiums: $306,368Surcharges with conversion: $26,857$333,226With conversion$193,305more Social Security kept
Total Medicare cost charged against the Social Security benefit over 26 years (ages 65–90), modeled in RetirementAdvisorPro. Standard Part B and Part D premiums are identical in both paths — $306,368. The entire $193,305 difference is the income-based surcharge (IRMAA), which is withheld from the Social Security check. Same gross benefit in both paths: $1,575,798. Assumes Part B premiums grow 7.3%/yr, Part D 6%/yr; single filer; the standard Part D premium is paid to the drug plan rather than withheld.

None of this says a conversion is right for any particular client, and nothing here recommends converting $500,000 in a single year — that shape is this scenario's, not a prescription. Converted in the wrong year, the first two mechanisms run in reverse: the conversion itself is ordinary income, so converting while collecting benefits maximizes the taxable share of the benefit that year and can trigger surcharges two years later. This scenario works because the conversion happens at 61 — before benefits, and far enough ahead of Medicare that the income spike never touches a premium.

What it does say: the decision is bigger than a tax-rate bet. For an advisor, the checklist looks like this.

  • Model Social Security net of Medicare, both paths. The gross benefit is identical by construction; the difference lives entirely below the line.
  • Project the MAGI that required distributions will create, and read the surcharge two years forward from the first spike.
  • Check the taxable-share window between RMD start and the 85% cap — that is where the tax leak concentrates.
  • For couples, run the plan as the survivor, not just as the couple. Single thresholds, one benefit gone.

Modeled in RetirementAdvisorPro: single filer, $4,500 monthly benefit at 65 with a 2% cost-of-living adjustment, $500,000 converted in one year at 61, required distributions from 75, projected to age 90. Every figure past 65 inherits the scenario's premium inflation assumptions — Part B at 7.3% a year (the sixty-year historical average), Part D at 6%. Lower assumptions shrink the late-year figures; they do not change the mechanisms, the thresholds, or the two-year lookback.

Disclaimer: This article is educational content for financial professionals. It is not investment, tax, legal, insurance, or accounting advice, and it is not a recommendation of any security, strategy, or product. Any examples, figures, and calculations are hypothetical illustrations based on the stated assumptions and on tax and Medicare rules in effect at the time of writing, which are subject to change; they are not predictions or guarantees, and individual results will differ. RetirementAdvisorPro is not a registered investment adviser, broker-dealer, insurance agency, law firm, or accounting firm, and nothing here creates an advisory or professional-client relationship. Consult a qualified financial, tax, or legal professional regarding your specific circumstances. See our full disclosures.

About the Author

Mark Annese

Mark Annese

Co-Founder of IRMAA Certified Planner, Founder of RetirementAdvisorPro

Mark Annese is an IRMAA Certified Planner specializing in helping financial advisors navigate Medicare income-related adjustments and optimize client retirement income strategies.

Frequently Asked Questions

Common questions about our platform and services

Does a Roth conversion affect Social Security benefits?

It never changes the benefit itself — the gross amount is set by the earnings record and claiming age. What it changes is how much of that benefit the retiree keeps. Roth withdrawals stay out of the income formula that decides how much of the benefit is taxable, and out of the income that sets Medicare's income-based surcharges, which are withheld from the Social Security payment. In the modeled scenario, the same $1,575,798 lifetime benefit delivers $193,305 more with the conversion than without it.

Does a Roth conversion increase taxes on Social Security in the year of the conversion?

It can, badly. The converted amount is ordinary income in the conversion year, so converting while collecting benefits can push the taxable share of the benefit to its 85% maximum and, two years later, trigger Medicare surcharges. That is why timing dominates: the modeled conversion happens at 61 — before benefits, and far enough before Medicare that the income spike never touches a premium.

Can a Roth conversion reduce IRMAA surcharges?

Yes, in later years. IRMAA is set by modified adjusted gross income from two years prior, and required minimum distributions are usually what push retirees over the thresholds. A conversion shrinks the account that generates those distributions. In the modeled scenario, lifetime surcharges fall from $220,162 to $26,857. The standard Part B premium is not reducible — everyone pays it — only the income-based surcharge on top of it.

Do Roth IRA withdrawals count toward the income that makes Social Security taxable?

No. The IRS formula counts one-half of benefits plus all other income, including tax-exempt interest — and traditional IRA distributions are ordinary income inside that formula. Qualified Roth distributions are excluded from gross income entirely, so they never enter it. That is the structural difference the conversion buys.

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