Don’t Wait Until December: 5 Tax Decisions Retirees Should Review Before the End of 2026
By Scott Searles | September 11th, 2026
December gets most of the attention when people talk about year-end tax planning.
I think September may be more valuable.
By this point in the year, you may have a reasonably good idea of your income, investment gains, retirement withdrawals, charitable giving, and other financial activity.
But unlike December, you still have time to evaluate your options.
For retirees and pre-retirees, that can be particularly important because taxes rarely exist in isolation.
A Roth conversion can affect taxable income.
Taxable income can affect Medicare premiums.
Investment gains can affect your tax bracket.
Retirement withdrawals can affect Social Security taxation.
And Required Minimum Distributions can change the equation again.
The goal isn’t simply to pay the least amount of tax this year. It’s to make tax decisions with your entire retirement in mind.
Here are five areas worth reviewing before 2026 gets away from us.
1. Is There Still a Roth Conversion Opportunity?
For retirees with significant balances in traditional IRAs and other tax-deferred retirement accounts, Roth conversions can be an important planning tool.
A Roth conversion generally involves moving money from a traditional IRA into a Roth IRA and recognizing the converted amount as taxable income in the year of conversion.
Why would anyone voluntarily create a tax bill?
Because sometimes paying taxes strategically today may help create greater tax flexibility later.
A conversion may be worth evaluating if you:
- Are temporarily in a lower tax bracket.
- Have retired but haven’t begun RMDs.
- Have a large traditional IRA balance.
- Want greater tax diversification.
- Are thinking about the taxes your heirs may eventually face.
But a Roth conversion isn’t automatically a good decision.
Converting too much could push income into a higher tax bracket, increase Medicare-related income, or create other unintended tax consequences.
The question shouldn’t be:
“Should I do a Roth conversion?”
A better question is:
“How much, if any, might make sense this year within my larger retirement tax strategy?”
That’s a very different analysis.
2. Don’t Let Your RMD Become a December Surprise
For retirees subject to Required Minimum Distributions, waiting until December to think about the requirement can unnecessarily limit planning flexibility.
RMDs generally create taxable income.
And once you’re required to take the distribution, you can’t simply convert the RMD itself to a Roth IRA.
That’s one reason we like to look at the entire retirement income picture before year-end.
For example:
How much income have you already received?
How much additional income do you expect?
Are there charitable intentions?
Could investment gains affect your tax situation?
Have you already satisfied your RMD?
For charitably inclined IRA owners who qualify, a Qualified Charitable Distribution, or QCD, may also be worth discussing.
A QCD generally allows an eligible IRA owner age 70½ or older to direct qualifying IRA distributions to eligible charities, subject to applicable rules and limits. A QCD can also count toward an RMD.
That can make charitable planning and retirement tax planning part of the same conversation.
3. Review Capital Gains Before the Calendar Runs Out
A strong year in the market can create a good problem:
Gains.
But gains can also create tax consequences.
By September, investors often have a clearer picture of what has happened inside taxable investment accounts.
That makes this a useful time to review:
- Realized capital gains.
- Unrealized gains.
- Investment losses.
- Concentrated positions.
- Planned portfolio changes.
- Charitable giving opportunities.
Tax-loss harvesting may sometimes help offset realized gains, although investment decisions shouldn’t be made solely for tax purposes.
The opposite can also be true.
There may be situations where intentionally recognizing a gain makes sense because of the taxpayer’s current income and capital-gains tax situation.
Again, the objective isn’t simply:
“How do I avoid a tax?”
It’s:
“When is the most strategic time to recognize income and gains?”
Sometimes the tax you intentionally pay can be just as important as the tax you avoid.
4. If You’re 65 or Older, Understand the New Senior Deduction
There is also an important tax provision retirees shouldn’t overlook.
Under current law, eligible taxpayers age 65 and older may qualify for an additional $6,000 senior deduction per person for tax years 2025 through 2028.
For a married couple where both spouses qualify, that can mean an additional deduction of up to $12,000.
The deduction begins phasing out when modified adjusted gross income exceeds $75,000 for an individual or $150,000 for married couples filing jointly.
Importantly, eligible taxpayers may claim the deduction whether they itemize or take the standard deduction.
For 2026, the regular standard deduction is also $16,100 for single filers and $32,200 for married couples filing jointly.
Why does all of this matter for planning?
Because deductions, income, Roth conversions, capital gains, and retirement distributions interact.
If you’re looking at any one of those decisions independently, you may be missing the larger picture.
5. Watch the Medicare Tax Ripple Effect
This is one of the areas retirees sometimes overlook.
Not every “tax” consequence shows up on your tax return.
Medicare’s Income-Related Monthly Adjustment Amount, better known as IRMAA, can cause higher-income Medicare beneficiaries to pay additional Part B and Part D premiums.
And Medicare generally uses income information from two years earlier when determining these surcharges.
That means a financial decision made in 2026 may potentially affect Medicare premiums in 2028.
Think about that for a moment.
A Roth conversion today.
A large capital gain today.
A substantial retirement distribution today.
Each could potentially have a financial consequence two years down the road.
That doesn’t mean you should avoid recognizing income.
Sometimes intentionally increasing taxable income may still make sense.
But the Medicare implications should be part of the calculation.
Tax planning isn’t just about your tax bracket.
It’s about understanding the ripple effects of the decisions you make.
The Bigger Opportunity: Think in Tax Windows, Not Tax Years
This is where retirement tax planning gets more interesting.
Imagine someone retires at 62.
Their paycheck disappears.
They don’t need Social Security immediately.
RMDs haven’t started.
Suddenly, there may be a period where taxable income is lower than it was during their working years—and potentially lower than it will be later in retirement.
I think of these periods as tax-planning windows.
During those windows, retirees may have opportunities to intentionally recognize income, convert retirement assets, realize gains, or reposition portions of their financial lives.
Those opportunities don’t necessarily last forever.
Social Security may begin.
RMDs may begin.
A spouse may die, potentially changing the surviving spouse’s filing status.
Tax laws may change.
That’s why retirement tax planning shouldn’t begin when your CPA starts preparing your return.
By then, much of the year is already history.
Scott’s Perspective
There’s a phrase I hear fairly often:
“We’ll worry about taxes at the end of the year.”
I think that’s backwards.
Your tax return looks backward.
Tax planning should look forward.
By December, many of the decisions that determined your tax situation have already been made.
September gives us something December doesn’t:
time.
Time to estimate income, to review gains, to evaluate a Roth conversion, to think about charitable giving, to coordinate an RMD.
And perhaps most importantly, time to ask whether reducing this year’s tax bill is actually the right objective.
Because I don’t necessarily want our clients to pay the lowest tax possible in 2026.
I want them thinking about how much tax they may pay over their lifetime.
Sometimes that means deferring income.
Sometimes it may mean intentionally recognizing income.
Sometimes it means doing absolutely nothing.
The strategy depends on the circumstances.
But waiting until the final week of December isn’t a strategy I’d want to rely on.
Why This Matters
Retirement creates a unique tax challenge.
You may have more control over your taxable income than you did while working—but that also means you have more decisions to make.
Traditional IRA withdrawals.
Roth conversions.
Social Security.
Investment gains.
Charitable giving.
RMDs.
Medicare premiums.
Each can affect another.
That’s why we believe tax planning and retirement income planning should be coordinated rather than treated as separate conversations.
At Skybox Financial Group, our focus is not simply on what your tax return looks like next April.
We want to understand what your tax picture could look like over the next 10, 20, or 30 years of retirement.
September may be one of the best times to start that conversation.
Frequently Asked Questions
Why should retirees do tax planning in September?
By September, retirees often have enough information to estimate annual income, investment gains, retirement distributions, and other tax items while still having time to evaluate potential year-end strategies.
Is a Roth conversion taxable in 2026?
Generally, amounts converted from a traditional IRA to a Roth IRA are included in gross income for the year of conversion, subject to applicable rules. Whether a conversion makes sense depends on the taxpayer’s broader financial and tax situation.
What is the additional senior deduction for 2026?
Eligible taxpayers age 65 or older may qualify for an additional deduction of up to $6,000 per person. For qualifying married couples where both spouses are eligible, the maximum is $12,000. The deduction begins phasing out above specified modified adjusted gross income levels.
Can a QCD satisfy an RMD?
A qualifying charitable distribution can generally count toward an eligible taxpayer’s Required Minimum Distribution when IRS requirements are met.
Can a Roth conversion increase future Medicare premiums?
Potentially. Roth conversions generally increase modified adjusted gross income in the conversion year, which may affect future Medicare IRMAA calculations for some beneficiaries.
Is There Still a Tax Opportunity Hiding in 2026?
The final months of the year can be an important planning period for retirees and pre-retirees.
Rather than waiting until December, now may be a good time to review your retirement income, investments, RMDs, Roth conversion opportunities, charitable plans, and potential Medicare implications.
Schedule a complimentary 15-Minute Strategic Phone Call with Scott Searles to discuss your questions and explore potential planning opportunities.
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440-238-6983
Sources:
Internal Revenue Service — 2026 Tax Inflation Adjustments
Internal Revenue Service — Enhanced Deduction for Seniors
DISCLOSURE
The information provided in this article is for general informational and educational purposes only and should not be construed as personalized investment, tax, or legal advice. Reading this material does not create an advisory relationship with Skybox Financial Group, LLC.
Investment advisory services are offered through Skybox Financial Group, LLC, an Ohio-registered investment adviser. Registration does not imply a certain level of skill or training. Advisory services are only offered to clients or prospective clients where Skybox Financial Group and its representatives are properly licensed or exempt from licensure. Insurance service provided by Skybox Risk Management, LLC.
All investments involve risk, including the possible loss of principal. Past performance is not indicative of future results. Any references to market performance, investment strategies, or financial planning concepts are provided for illustrative purposes only and may not be appropriate for your individual situation.
Before implementing any strategy discussed, you should consult with a qualified financial professional to determine its suitability based on your specific financial circumstances and objectives.
