May is one of the most action-packed months on the retirement financial calendar, and getting organised now — while April is fresh in your mind — can save you real money and headaches. Whether you missed a deadline in April, need to catch up on required minimum distributions (RMDs), or want to get ahead of Medicare costs for next year, May gives you a valuable window to reset, review, and act. Here is exactly what to put on your calendar, and why each item matters for your bottom line.

What financial tasks should I carry over from April?

April is tax month, and the dust has likely just settled. Before you file April away entirely, do a quick review of three things: whether you filed or extended your federal return, whether you made any IRA contributions for the 2025 tax year, and whether your tax bill gave you any surprises that point to a planning gap.

If you filed an extension, your return is now due October 15 — but any taxes owed were still due April 15. If you underpaid, interest is already accruing, so addressing that early in May is worth a phone call to your tax preparer.

If your 2025 return showed more taxable income than expected — especially from Social Security or retirement account withdrawals — May is the right time to start adjusting your 2026 withholding or estimated tax payments.

How much of Social Security is taxable, and how do I plan around it?

This surprises many retirees: 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 nontaxable interest, plus half of your Social Security benefits). If that combined figure exceeds $34,000 for single filers or $44,000 for married couples filing jointly, 85% of your benefit is taxable.

If your April tax return showed a big Social Security tax bill, May is the time to look at strategies like Roth conversions (moving money from a traditional IRA to a Roth IRA while managing which tax bracket you land in), timing of other income, or adjusting voluntary tax withholding directly from your Social Security payments using IRS Form W-4V.

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

Required minimum distributions — the annual withdrawals the IRS requires you to take from traditional IRAs, 401(k)s, and most other tax-deferred retirement accounts — are a May concern for two reasons.

First, if you turned 73 in 2025, you had the option to delay your very first RMD until April 1, 2026. If you took that delay, your first RMD was due by April 1, and your second RMD for 2026 is due by December 31. That means you could owe two RMDs in one year, which could push you into a higher tax bracket. If this is your situation, run the numbers now — taking the second distribution earlier in the year (say, in May or June) can spread the tax impact more evenly.

Second, for everyone already taking annual RMDs, May is a good checkpoint to confirm you are on track to meet your full 2026 obligation before the year-end rush. Missing an RMD carries a 25% excise tax on the amount you should have withdrawn — a penalty that is entirely avoidable with a little calendar discipline.

How do I avoid Medicare IRMAA surcharges?

IRMAA stands for Income-Related Monthly Adjustment Amount — it is the extra premium higher-income Medicare enrollees pay on top of the standard Part B and Part D premiums. For 2026, if your 2024 income (which is what Medicare uses for this year’s calculation) exceeded $106,000 for individuals or $212,000 for couples, you are likely paying IRMAA surcharges right now.

Here is why May matters: if your income dropped significantly in 2025 — because you retired, sold a business, or had another life change — you can appeal your IRMAA using IRS Form SSA-44. You do not have to wait for Medicare to automatically recalculate based on your 2025 return. Filing that appeal sooner rather than later means you could see reduced premiums faster.

For those not yet in IRMAA territory, this is the moment to look at your 2026 income picture. Roth conversions, large asset sales, or high RMDs can all push you over the threshold. A conversation with a financial planner or tax advisor in May — before mid-year income events happen — gives you the most options.

What is the Medicare Part B premium in 2025 and what should I expect?

The standard Medicare Part B premium for 2025 is $185.00 per month, up from $174.70 in 2024. Most people have this deducted automatically from their Social Security payment. If you are not yet receiving Social Security and pay your premium directly, confirm your payment method is current — a missed Part B payment can result in a coverage gap.

For 2026 premiums, Medicare has not yet finalised numbers at the time of publication, but they are typically announced in the fall. Keeping an eye on that announcement (we will cover it in Silver & Cents when it drops) helps you budget accurately for next year.

When should I claim Social Security to maximise my benefit?

This is one of the most searched questions in retirement planning — and for good reason. The short answer: every year you delay claiming Social Security past your full retirement age (which is 67 for anyone born in 1960 or later), your benefit grows by approximately 8% per year, up until age 70. That is a guaranteed, inflation-adjusted return that is very hard to beat.

If you have not yet claimed and are between ages 62 and 70, May is a good time to request your personalised Social Security statement at ssa.gov to see your projected benefit at different claiming ages. If you are already claimed and wondering whether you made the right call — most of the time, the best move now is to optimise around your existing benefit rather than dwell on past decisions.

For married couples, the higher earner delaying to 70 also maximises the survivor benefit — an often-overlooked factor that can make a huge difference for a surviving spouse’s financial security.

Your May financial checklist at a glance

Here is a simple list to work through this month:

  • Review your April tax return for surprises and adjust 2026 withholding if needed
  • Confirm your 2026 RMD amount and schedule withdrawals to avoid a year-end crunch
  • Check for IRMAA on your Medicare bill and appeal if your income dropped in 2025
  • Verify your Medicare Part B payment method is current
  • Pull your Social Security statement at ssa.gov if you have not claimed yet
  • Talk to a tax advisor about Roth conversions before mid-year income events

Retirement finances reward the people who stay one step ahead. May is your chance to do exactly that.

Frequently Asked Questions

When should I claim Social Security to maximise my benefit?

For most people, delaying Social Security until age 70 produces the largest possible monthly benefit, because benefits grow roughly 8% for each year you delay past your full retirement age (67 for those born in 1960 or later). If you are in good health and can cover living expenses from other sources, waiting typically pays off — especially for the higher earner in a married couple, since delaying also maximises the survivor benefit.

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 (adjusted gross income plus nontaxable interest plus half your Social Security) exceeds $34,000 for single filers or $44,000 for married couples filing jointly. Below those thresholds, either 0% or 50% of your benefit is taxable. Note that some states also tax Social Security, so check your state rules.

What are the RMD rules for 2025 and 2026?

Required minimum distributions must be taken annually from traditional IRAs and most employer retirement accounts once you reach age 73. For 2026, the deadline for your annual RMD is December 31, with one exception: if you turned 73 in 2025 and delayed your first RMD, it was due April 1, 2026, and your second RMD is still due December 31, 2026. Missing an RMD triggers a 25% excise tax on the amount not withdrawn.

How do I avoid Medicare IRMAA surcharges?

IRMAA surcharges are based on your income from two years prior, so the best long-term strategy is managing taxable income — for example, using Roth conversions, timing asset sales, and spreading RMDs across years to stay below the thresholds ($106,000 single / $212,000 married for 2026). If your income dropped significantly due to a life event such as retirement or divorce, you can file IRS Form SSA-44 to appeal your IRMAA and potentially reduce your premium sooner.

What is the Medicare Part B premium for 2025?

The standard Medicare Part B premium for 2025 is $185.00 per month, which represents an increase from $174.70 in 2024. Higher-income enrollees pay more due to IRMAA surcharges. The 2026 premium is typically announced in the fall; most enrollees have the premium automatically deducted from their Social Security payment each month.