May is one of the most action-packed months of the year for retirees and near-retirees. Between Social Security timing decisions, required minimum distribution (RMD) rules that changed again in 2026, Medicare premium traps to sidestep, and mid-year tax planning, the next 31 days offer a real opportunity to protect — and even grow — your retirement income. Here is exactly what to add to your May financial calendar so nothing slips through the cracks.

Why does May matter so much for retirement finances?

April gets all the attention because of Tax Day, but May is when the smart money moves happen quietly. The dust has settled on your 2025 tax return, you have a clear picture of last year’s income, and you still have seven months left in 2026 to course-correct. That combination makes May the ideal window to revisit Social Security strategy, check your RMD progress, and audit your Medicare situation before the fall enrollment season creeps up.

When should you claim Social Security to maximise your benefit?

If you have been putting off this decision, May is a great time to run the numbers again. Here is the plain-English version: every month you delay claiming Social Security past your full retirement age (FRA) — which is 67 for anyone born in 1960 or later — your monthly benefit grows by roughly 0.67%, or about 8% per year, up until age 70. Claim at 62 and you could permanently reduce your benefit by as much as 30%.

That said, “delay as long as possible” is not the right answer for everyone. Your health, whether you are still working, a spouse’s benefit, and your other income sources all factor in. Use May to book a free appointment with your local Social Security Administration office or use the SSA’s online Retirement Estimator at ssa.gov. A one-hour conversation now can be worth tens of thousands of dollars over a 20-year retirement.

How much of Social Security is taxable — and how do you reduce it?

This surprises a lot of people: up to 85% of your Social Security benefit can be subject to federal income tax, depending on your “combined income” (that is your adjusted gross income, plus any tax-exempt interest, plus half of your Social Security benefit). If that combined figure is above $34,000 for single filers or $44,000 for married couples filing jointly, expect 85% of your benefit to be taxable.

The May move: look at your 2025 tax return and calculate where you landed. If you are close to one of those thresholds, strategies like Roth conversions, timing of IRA withdrawals, or harvesting investment losses can help keep more of your benefit out of the IRS’s reach in 2026. A tax professional who specialises in retirement income — not just filing returns — is worth every penny here.

What are the RMD rules you need to know for 2026?

Required minimum distributions — the annual withdrawals the IRS requires you to take from traditional IRAs and most employer retirement accounts — have gone through significant changes in recent years, and 2026 has a few nuances worth noting.

The big picture: if you turned 73 in 2025 or earlier, you are already in RMD territory. If you turn 73 in 2026, your first RMD is due by April 1, 2027 — but waiting until then means you will have to take two distributions in 2027, which could push you into a higher tax bracket. Many financial planners recommend taking your first RMD in the year you turn 73, rather than using that April 1 extension, precisely to avoid that double-hit.

Your RMD amount is calculated by dividing your account balance (as of December 31 of the prior year) by an IRS life expectancy factor. Your financial institution should provide this calculation, but it is always worth double-checking. Failing to take your full RMD triggers a 25% excise tax on the amount you missed — reduced to 10% if you correct the mistake quickly, but still painful. Put a May reminder on your calendar to confirm your 2026 RMD amount and set up automatic distributions if you have not already.

How do you avoid Medicare IRMAA surcharges?

IRMAA stands for Income-Related Monthly Adjustment Amount — it is the extra premium higher-income Medicare beneficiaries pay on top of the standard Part B and Part D premiums. For 2026, the standard Medicare Part B premium is $185.00 per month. But if your income from two years ago (meaning your 2024 tax return, which Medicare uses to set 2026 premiums) exceeded $106,000 as a single filer or $212,000 as a married couple, you are already paying more.

The May action item: if you had a significant income drop in 2025 — retirement, job loss, divorce, or death of a spouse — you can appeal your IRMAA surcharge using Form SSA-44. Do not assume you are stuck with premiums based on old income. Also, if your 2026 income is tracking higher than expected, look at ways to bring it down before December 31: qualified charitable distributions (QCDs) from your IRA, bunching deductions, or delaying a Roth conversion to next year. Every dollar you keep under an IRMAA threshold saves you real money every single month.

What else belongs on your May financial calendar?

Beyond the big four above, here are a few quick wins to schedule this month:

  • Review your Medicare Advantage or Medigap plan. You cannot switch plans mid-year without a special enrollment period, but May is a good time to document any coverage frustrations so you are ready to act during the Annual Enrollment Period that opens October 15.
  • Check your beneficiary designations. IRAs, 401(k)s, and life insurance policies pass outside your will, so outdated beneficiary forms can override your wishes entirely. If your will is outdated or missing, use a basic trust and will creation tool as a starting checklist before an attorney review.
  • Look at your emergency fund. Financial planners typically suggest retirees keep one to two years of essential expenses in cash or short-term CDs. With rates still relatively favorable, May is a good time to shop for better yields on savings you are already holding.
  • Shred old documents. You generally need to keep tax returns for three years (seven if you underreported income), so 2022 and older returns can now be safely destroyed.

May is the month where preparation quietly pays off. The retirees who do this kind of mid-year check-in consistently end up with fewer surprises at year-end — and often keep thousands of dollars they would otherwise have handed over in taxes, surcharges, or penalties.

Frequently Asked Questions

Frequently Asked Questions

When should I claim Social Security to maximise my benefit?

Delaying Social Security past your full retirement age (67 for those born in 1960 or later) increases your monthly benefit by about 8% per year, up to age 70. However, the best claiming age depends on your health, marital status, and other income sources, so run a personalised estimate at ssa.gov before deciding.

How much of my Social Security benefit is taxable?

Up to 85% of your Social Security benefit may be subject to federal income tax if your combined income exceeds $34,000 (single) or $44,000 (married filing jointly). Combined income is your adjusted gross income plus tax-exempt interest plus half of your Social Security benefit. Strategic Roth conversions or timing of IRA withdrawals can help keep you below these thresholds.

What are the RMD rules for 2025 and 2026?

Required minimum distributions begin at age 73 under current law. Your RMD amount is calculated by dividing your prior year-end account balance by an IRS life expectancy factor, and your financial institution should provide this figure. Missing an RMD triggers a 25% excise tax on the shortfall, reduced to 10% if corrected promptly.

How do I avoid Medicare IRMAA surcharges?

IRMAA surcharges are based on your income from two years prior, so managing your taxable income proactively is the best defence. If your income dropped significantly due to retirement, divorce, or a spouse’s death, you can appeal your surcharge using IRS Form SSA-44. Strategies like qualified charitable distributions and delaying Roth conversions can also help keep income below IRMAA thresholds.

What is the Medicare Part B premium for 2025 and 2026?

The standard Medicare Part B premium for 2026 is $185.00 per month. Higher-income beneficiaries pay additional IRMAA surcharges on top of this amount, starting when individual income exceeds $106,000 or joint income exceeds $212,000 based on the prior-prior year tax return.