A Year-Round Tax Checklist for Retirees

By Tom, CPA · Updated October 27, 2026

Part of: Tax Planning

TL;DR: Set up withholding or estimates, take RMDs from 73, and use QCDs from 70 1/2 to give from your IRA without raising AGI. Claim the extra standard deduction and the $6,000 senior deduction through 2028, watch IRMAA’s two-year lookback, and plan conversions each fall.

Educational only, not tax, legal, or investment advice. Examples are illustrations, not predictions. Rules and limits change; verify current figures and talk to a qualified professional about your situation.

The tax code is 4 million words long, and retirement is when you finally have time to read them, which is unfortunate, because retirement is also when they get more complicated. Paychecks stop, but withholding, Medicare premiums, required distributions and Social Security taxation start. Retirees also have more control over their taxable income than at any other time, which makes a checklist worth the effort. Figures are for 2026, as of Oct 2026.

CPA Warning Label: Missed RMDs carry a 25% penalty, and large conversions can raise Medicare premiums two years later. Confirm figures for your situation before acting.

The year you retire

• Plan the final paycheck year. Your last working year often has a full salary plus payouts for vacation, bonuses or severance. Defer what you can into the 401(k) before leaving, and avoid stacking large IRA withdrawals or Roth conversions on top.
• Decide what to do with the 401(k). Leaving it in the plan keeps Rule of 55 access if you separated in or after the year you turned 55. Rolling to an IRA gives more investment choice. Keep after-tax basis records either way.
• Choose a Social Security start date. Each year of delay past full retirement age raises benefits until 70, and the years before claiming are often ideal for Roth conversions at low brackets.
• Line up health coverage. Medicare starts at 65; enroll on time to avoid lifetime late penalties. Before 65, ACA marketplace credits depend on MAGI.
• Start a tax-year spreadsheet projecting income, brackets and thresholds for each year until RMDs begin.

Every January

• Set up withholding or estimates. Retirees often owe because nothing is withheld. Use Form W-4P for pensions and other periodic payments, Form W-4R for one-off IRA withdrawals, Form W-4V for Social Security (7%, 10%, 12% or 22%), or quarterly estimated payments. A trick: take a large IRA distribution late in the year with heavy withholding, which counts as paid evenly through the year.
• Check Medicare premiums. IRMAA surcharges use your tax return from two years earlier. If income dropped because you retired, file Form SSA-44 with Social Security to request a redetermination. See IRMAA planning.
• Gather 1099-R, SSA-1099 and brokerage forms. Confirm rollovers are coded correctly.

Required minimum distributions

• Know your start age. RMDs from traditional IRAs and 401(k)s begin at 73 for those reaching 72 after 2022 (Publication 590-B). The first RMD can be delayed to April 1 of the following year, but then two RMDs land in one year.
• Still working? You can usually delay RMDs from your current employer's plan until you retire, unless you own more than 5% of the company. IRAs have no such exception.
• Roth IRAs have no lifetime RMDs, and from 2024 neither do Roth 401(k)s.
• Missed an RMD? The penalty is 25% of the shortfall, reduced to 10% if corrected promptly. File Form 5329 and request a waiver for reasonable cause.
• Inherited IRAs have their own rules, often a 10-year payout.

Charitable giving

• Qualified charitable distributions (QCDs) from an IRA at age 70½ or older go directly to charity, up to $111,000 in 2026. They count toward your RMD and never enter AGI, which helps with Social Security taxation, IRMAA and the senior deduction phaseout.
• Non-itemizer deduction: from 2026, those taking the standard deduction can deduct up to $1,000 ($2,000 joint) of cash gifts to operating charities, not donor-advised funds.
• Itemizers face a new 0.5% of AGI floor from 2026; bunching gifts can help.

Deductions and credits for seniors

• Standard deduction of $32,200 joint or $16,100 single for 2026, plus an additional amount for each person 65 or older or blind.
• Senior deduction: $6,000 per person 65+ for 2025 through 2028, whether or not you itemize, phasing out above $75,000 MAGI single or $150,000 joint.
• Medical expenses above 7.5% of AGI, including Medicare premiums and age-based long-term care insurance premium limits ($6,200 per person over 70 in 2026). See the medical expense deduction.
• Social Security taxation: up to 85% of benefits can be taxable depending on provisional income (Publication 915). These thresholds are not indexed.

Illustration: QCD vs cash gift

Illustration: a married couple, both 74, take the standard deduction. Their RMD is $40,000 and they give $10,000 to charity each year.

The QCD reduces taxable income by $8,000 more. At 12%, that is about $960 a year, plus a lower AGI that can reduce taxable Social Security and keep them further from IRMAA tiers.

QCDs must go directly from the IRA custodian to the charity. A check made out to you and then donated does not qualify. Assumptions: gifts go to qualifying public charities, not donor-advised funds; no state effects.

Every fall

• Project the year's income and decide on Roth conversions, gain harvesting or extra IRA withdrawals to fill a target bracket. The 0% long-term capital gain rate applies up to $98,900 of taxable income joint in 2026.
• Take the RMD and any QCDs before December 31.
• Review health coverage during open enrollment. Early retirees on ACA plans should check subsidy effects. See the ACA and Medicaid gap.
• Consider annuity tax treatment if buying one. See annuities for early retirees.
• Review real estate and gains. See the real estate tax checklist and capital gains planning.
• Update beneficiaries and confirm estate documents.
• Harvest losses in taxable accounts if markets fell, to offset gains or up to $3,000 of ordinary income.
• Check next year's estimated payments so the January plan starts with real numbers.

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