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The retirement tax checklist: what to check before and after you retire

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Once your income comes from Social Security, an IRA and maybe a pension, the tax rules change and the breaks are claimed, not handed to you. Here is the list to work through every year.

November 3, 2026
Adjunct Professor of Finance, Johns Hopkins University Carey Business School · Author, The Social Security Playbook

Key takeaways

  • Provisional income, your other income plus half your Social Security, decides how much of your benefit is taxable.
  • A large IRA withdrawal or Roth conversion can push you over a threshold and raise Medicare premiums two years later.
  • Confirm the 65+ deductions you qualify for are on your return, adjust withholding with Form W-4V, and use free TCE or VITA help.

You are retired, or close to it, and your income now arrives from several places: Social Security, an IRA, maybe a pension. Each is taxed differently, and the breaks that lower the bill are claimed, not applied for you. Run this checklist once a year, before you file and before any large withdrawal.

How much of your Social Security is taxable?

The federal tax on Social Security is decided by one number. The Retirement Tax Checklist, our fact-checked guide, defines provisional income as your other income plus half of your Social Security benefit.

The thresholds are fixed by law. Single filers: under $25,000, none of the benefit is taxable; $25,000 to $34,000, up to 50% is taxable; over $34,000, up to 85%. Married filing jointly: under $32,000, none; $32,000 to $44,000, up to 50%; over $44,000, up to 85%.1

As the guide puts it, 85% is not a tax rate but the most of your benefit that can count as taxable income; at least 15% stays tax-free.

If you expect to owe tax on your benefit, you can have it withheld rather than face a bill in April; if too much is already coming out, you can right-size or stop it. Either way the form is IRS Form W-4V.3 The goal, in the guide’s words: pay what you owe, not a dollar more.

How do withdrawals, RMDs, Roth conversions and the QCD affect your taxes?

A large IRA withdrawal or a Roth conversion counts as income in the year you take it, which can push provisional income over a threshold and raise the tax on your benefit at the same time. Once required minimum distributions begin, you cannot avoid the amount, but you control when in the year it comes out and whether part of it goes to charity (below). Spreading a Roth conversion across several tax years keeps each year’s income lower.

The guide notes that Medicare adds the IRMAA surcharge to Part B and Part D premiums for incomes above $109,000 single or $218,000 joint, based on your tax return from two years earlier. A one-time spike means higher premiums two years later. If one of the life-changing events listed on Form SSA-44 has since lowered your income, such as stopping or cutting back work, marriage, divorce or a spouse’s death, file the form to have the surcharge recalculated; an income drop on its own, without one of the listed events, does not qualify.6

If you are 70½ or older and give to charity anyway, the guide singles out the qualified charitable distribution. Money goes directly from your IRA custodian to a qualified charity, up to $111,000 in 2026, and never appears as taxable income.8 It can satisfy your RMD, and because the amount stays out of your adjusted gross income instead of being added to it the way an ordinary withdrawal would be, it can reduce how much of your Social Security is taxed and help you stay under an IRMAA line.5 It must be a direct transfer from the IRA custodian to the charity, not to a donor-advised fund, and if you made deductible IRA contributions after age 70½, those reduce the amount you can exclude.

Which deductions can you claim at 65 and older?

Two separate breaks stack on top of your standard deduction, and the guide reports both get missed. The Senior Deduction is $6,000 per person 65 or older, $12,000 if both spouses qualify, with no need to itemize.4 You get the full amount with modified adjusted gross income up to $75,000 single or $150,000 joint; above that it shrinks by 6% of the excess income for each eligible person, which phases it out completely at $175,000 single and $250,000 joint. You must be 65 by the end of the tax year and have a valid Social Security number, and a married couple must file jointly; married filing separately does not qualify.

The second is the permanent extra standard deduction for 65+: $2,050 for a single filer, $1,650 per spouse. The Senior Deduction is available whether you itemize or take the standard deduction; the extra standard deduction is only for those who take the standard deduction, so if you itemize you get one break, not both.

The deadline on this list. The guide reports the Senior Deduction applies to tax years 2025 through 2028 only, unless Congress extends it. Confirm your software or preparer actually applied it, every year it exists.

If you itemize, medical costs above 7.5% of your adjusted gross income are deductible, and the guide notes Medicare premiums count toward that floor.

Then the state return. States differ on whether they tax Social Security, pensions and retirement withdrawals at all, and some that do exempt them below an income limit. Check your state revenue department’s rules for retirees rather than assuming.

What should you do next?

  1. Add up your provisional income before any IRA withdrawal or Roth conversion, and compare it with the thresholds for your filing status.
  2. If you expect to owe, or are overpaying, file Form W-4V to adjust withholding.
  3. Before a large withdrawal or conversion, check whether splitting it across two tax years keeps you under a threshold or an IRMAA line.
  4. If you are 70½ or older and give to charity, ask your IRA custodian to send the gift directly as a QCD.
  5. Confirm the 65+ deductions you qualify for are on your return: the Senior Deduction either way, the extra standard deduction only if you do not itemize.
  6. If one of the life-changing events listed on Form SSA-44 lowered your income, file it with proof to ask SSA to recalculate IRMAA.
  7. For a standard retirement return, use free IRS-trained help: TCE (focused on taxpayers 60 and older, mostly run by AARP Foundation Tax-Aide, 888-227-7669) or VITA (the IRS sets no program-wide income limit, though individual sites may set their own, 800-906-9887).7
Kwame Kuadey
Fact-checked against primary sources. Every figure in this piece was checked against the agency or study that publishes it, and independently verified on November 7, 2026. Last reviewed November 7, 2026. Spotted something? hello@benefitsinsider.co
From Next Chapter TodayFifteen free guides to the decisions that cost the most.Social Security claiming, Medicare enrollment, SNAP paperwork, taxes in retirement. Fact-checked, printable.Browse the guides →

Next Chapter Today is not a government website and is not affiliated with the Social Security Administration or any agency. This article is educational and is not individualized legal, medical, tax or financial advice. Confirm your own figures with the agency before you act.

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