A Strategic Guide for High-Net-Worth Retirees

As the April 15 filing deadline approaches, most taxpayers are focused on getting documents organized and returns submitted. But for high-net-worth individuals nearing or already in retirement, March is not just about compliance; it is one of the final opportunities to influence your 2025 tax outcome and proactively position your 2026 strategy.

The returns you file by April 15, 2026, will reflect your 2025 tax year, but the decisions you make now can also shape your 2026 and 2027 tax picture, including future Medicare premiums and required minimum distributions.

Tax planning at this level is rarely about basic deductions. It is about income timing, bracket management, Medicare premium exposure, estate planning alignment, and preserving after-tax wealth over decades, not just one filing cycle.

If you are approaching retirement or already living on portfolio income, here are the most important last-minute tax strategies to evaluate before April 15.

1. Maximize 2025 IRA Contributions Before the Deadline

Even though the 2025 tax year has ended, you may still be able to make contributions that reduce taxable income, but only until April 15, 2026.

For 2025, the combined contribution limit across all your IRAs is 7,000 if you are under age 50, and 8,000 if you are 50 or older, assuming you have enough earned income and meet the IRS eligibility rules.

Traditional IRA Contributions

If you (or your spouse) had earned income in 2025, you may still qualify for a deductible traditional IRA contribution. For high-income earners, deductibility may phase out depending on:

• Income levels
• Participation in an employer-sponsored retirement plan

Even if not deductible, non-deductible contributions may open the door to strategic Roth conversions (more on that below).

Roth IRA Contributions

Direct Roth IRA contributions are subject to income limits. However, high-net-worth individuals often utilize the Backdoor Roth IRA strategy, which involves:

1. Making a non-deductible traditional IRA contribution
2. Converting those funds to a Roth IRA

If executed properly and with attention to the pro-rata rule, this strategy can continue building tax-free retirement assets.

If you already have sizable pre-tax IRA balances, the pro-rata rule can make each conversion more taxable than expected, which is why coordinating backdoor Roth strategies with your advisor and CPA is essential.

2. SEP IRA and Solo 401(k) Contributions for Business Owners

If you retired recently but had self-employment income in 2025, consulting, board work, real estate activity, or business ownership, you may still have time to contribute to:

• SEP IRA
• Solo 401(k)

Depending on your filing structure, contributions may be allowed up until the tax filing deadline (including extensions).

For high earners, these contributions can materially reduce 2025 taxable income, even after the calendar year has ended.

3. Review Required Minimum Distributions (RMDs) for 2025

Under the SECURE 2.0 framework, RMD age thresholds have shifted:

• Age 73 for individuals born between 1951 and 1959
• Age 75 beginning in 2033

If 2025 was your first RMD year, you may have delayed the initial distribution until April 1, 2026. However, doing so requires careful planning.

Taking your first RMD in 2026 means you will have to take two distributions in 2026: one by April 1, 2026, for your 2025 RMD, and another by December 31, 2026, for your 2026 RMD. That can:

• Push more income into a single tax year
• Compress you into a higher tax bracket
• Increase the risk of higher Medicare IRMAA surcharges

If you delayed your first RMD, now is the time to model the tax impact before executing.

Also, confirm that all required 2025 RMDs were completed correctly. While penalties have been reduced under recent law, compliance remains essential.

4. Analyze Medicare IRMAA Exposure

High-net-worth retirees are often surprised by Medicare premium surcharges.

Medicare IRMAA (Income-Related Monthly Adjustment Amount) is triggered by income reported two years prior. That means your 2025 income determines your 2027 Medicare premiums.

Before filing your 2025 return, evaluate whether:

• Large capital gains
• Roth conversions
• Business sales
• Unexpected income spikes

As these may push you into a higher IRMAA tier.

For instance, realizing an additional six‑figure capital gain in 2025 could move a couple into a higher IRMAA tier in 2027, increasing their combined Medicare premiums by thousands of dollars over just a few years.

Strategic income smoothing, particularly in early retirement, can help you save thousands in future Medicare premiums.

5. Confirm Safe Harbor Estimated Tax Compliance

Underpayment penalties can apply even to wealthy retirees if estimated payments were not handled correctly.

The IRS safe harbor rules generally allow you to avoid penalties if you paid during the year the lesser of:

• 90% of the tax you ultimately owe for the current year, or
• 100% of your prior year’s total tax (110% if your adjusted gross income exceeded 150,000, or 75,000 if married filing separately).

High-income retirees with volatile investment income should confirm compliance before filing.

If needed, you may still be able to adjust withholding on IRA distributions before filing to correct shortfalls.

6. Revisit Roth Conversion Strategy for 2026

While Roth conversions for 2025 must have been completed by December 31, March is an ideal time to plan 2026 conversions.

Now that your 2025 numbers are mostly known, you can:

• Identify your effective tax bracket
• Determine how much room exists in your current bracket
• Strategically convert portions of tax-deferred assets

For high-net-worth retirees, Roth conversions can:

• Reduce future RMD exposure
• Decrease lifetime tax liability
• Simplify estate planning
• Provide tax-free assets to heirs

The key is precision, not aggressive conversion without modeling.

7. Evaluate Capital Gains Positioning

Now is also an excellent time to assess how 2025 investment decisions impacted your tax position.

Review:

• Realized gains and losses
• Carryforward losses
• Concentrated stock exposure
• Unrealized appreciation

For retirees living off portfolio income, after-tax returns matter significantly more than nominal returns.

If you anticipate large liquidity events in 2026, such as real estate sales or business exits, proactive capital gains planning now can help mitigate future tax shocks.

8. Estate and Gift Planning Under Current Exemption Levels

As of 2026, the federal estate and gift tax exemption remains historically high—on the order of roughly 15 million per person and indexed for inflation—but Congress can and has changed these thresholds over time, so high‑net‑worth families should review their plans regularly.

For high-net-worth families, this creates both opportunity and uncertainty.

Now is a smart time to:

• Review trust structures
• Confirm beneficiary designations
• Evaluate lifetime gifting strategies
• Consider using annual exclusion gifts

Advanced techniques such as:

• Spousal Lifetime Access Trusts (SLATs)
• Grantor Retained Annuity Trusts (GRATs)
• Irrevocable Life Insurance Trusts (ILITs)

should be reviewed in light of your net worth trajectory and legislative risk tolerance.

Even if your estate falls below federal thresholds, state-level estate taxes may still apply.

9. Charitable Giving Strategy Review

Charitable planning remains one of the most tax-efficient tools available to high-net-worth retirees.

Consider whether your 2025 giving was optimized through:

• Qualified Charitable Distributions (QCDs)
• Donor-advised funds
• Appreciated stock donations

If QCDs were not utilized and you are eligible (age 70½+), it may be worth incorporating them into your 2026 plan.

For 2026, you can generally direct up to 111,000 per person in Qualified Charitable Distributions from IRAs to eligible charities, or up to 222,000 for a married couple if both spouses qualify, and these amounts are indexed for inflation over time.

Donating appreciated securities rather than cash can eliminate capital gains tax while still generating a charitable deduction.

10. Social Security Tax Optimization

Up to 85% of Social Security benefits may be taxable depending on provisional income.

If 2025 income was unusually high due to:

• Asset sales
• Roth conversions
• Deferred compensation payouts

This may increase your Social Security taxation.

This reinforces the importance of multi-year income planning rather than single-year decision-making.

Plan for the 2026 Tax Year — Not Just Filing 2025

Now is not the time to be reactive. It should be strategic.

Ask:

• Is your retirement income diversified across tax buckets?
• Are you intentionally managing bracket exposure?
• Is your withdrawal strategy aligned with longevity projections?
• Are you coordinating tax strategy with estate planning?

High-net-worth retirees who treat tax planning as a year-round process often preserve significantly more wealth over time.

Final March Checklist for High-Net-Worth Retirees

Before April 15, confirm that you have:

• Made all eligible IRA contributions
• Evaluated backdoor Roth opportunities
• Confirmed RMD compliance
• Reviewed Medicare IRMAA exposure
• Verified estimated tax safe harbor compliance
• Assessed Roth conversion strategy for 2026
• Reviewed capital gains positioning
• Updated estate planning documents
• Evaluated charitable optimization

The Strategic Advantage of Proactive Planning

At higher net worth levels, tax inefficiency compounds quickly. A poorly timed withdrawal, unnecessary RMD delay, unmanaged capital gain, or uncoordinated estate strategy can cost hundreds of thousands, sometimes millions, over a lifetime.

Tax strategy is not separate from retirement planning. It is integral to:

• Income sustainability
• Wealth preservation
• Legacy efficiency
• Multigenerational planning

At Agemy Financial Strategies, we work alongside your CPA and estate attorney to help ensure that tax decisions align with your broader retirement objectives.

If you would like a coordinated pre–April 15 review of your tax position and forward-looking strategy, we encourage you to schedule a planning session now. The most valuable tax moves are rarely truly last-minute, but the weeks leading up to April 15 still offer a meaningful window to refine your plan.

Contact us today at agemy.com. 

Investment advisory services are offered through Agemy Wealth Advisors, LLC, a Registered Investment Advisor and fiduciary to its clients. Agemy Financial Strategies, Inc. is a franchisee of Retirement Income Source®, LLC. Agemy Financial Strategies, Inc. and Agemy Wealth Advisors, LLC are associated entities. Agemy Financial Strategies, Inc. and Agemy Wealth Advisors, LLC entities are not associated with Retirement Income Source®, LLC. The information contained in this e-mail is intended for the exclusive use of the addressee(s) and may contain confidential or privileged information. Any review, reliance or distribution by others or forwarding without the express permission of the sender is strictly prohibited. If you are not the intended recipient, please contact the sender and delete all copies. To the extent permitted by law, Agemy Financial Strategies, Inc and Agemy Wealth Advisors, LLC, and Retirement Income Source, LLC do not accept any liability arising from the use or retransmission of the information in this e-mail.