Year-End Tax Planning Checklist for Pre-Retirees and Retirees (2026)

Quick Answer: Most year-end tax moves for people approaching or in retirement have a hard deadline of December 31, 2026. The six items worth reviewing are: workplace plan and catch-up contributions, HSA contributions, a possible Roth conversion, required minimum distributions (RMDs), qualified charitable distributions (QCDs), and a check on your taxable account and tax withholding. Which of these matter for you depends on your age, income, and the accounts you hold, which is why we walk through them as a set rather than one at a time.

Why Year-End Matters More Than Most People Realize

Tax planning has a way of showing up in March, when the return is already being prepared and most of the options are gone. By then, the decisions that shape your 2026 tax bill have already been made, whether or not anyone made them on purpose.

The weeks between now and December 31 are when you still have choices. Some moves, like Roth conversions and RMDs, have to be completed by year-end. Others, like IRA and HSA contributions, can generally be made up to the tax filing deadline, but payroll-based contributions run out when your last paycheck of the year does.

For our clients in Valparaiso, across Northwest Indiana, and throughout the Greater Chicagoland area, we like to treat this as a short annual review rather than a scramble. Below is the checklist we use as a starting point. It's organized into moves that tend to matter most for pre-retirees and moves that tend to matter most for retirees, though there's plenty of overlap.

A note before we start: this is general education, not tax advice or a recommendation for your situation. Tax rules have exceptions, and your CPA or tax professional should confirm how any of this applies to you.

For Pre-Retirees (Roughly Ages 55 to 65)

1. Review Your Workplace Plan Contributions

For 2026, the 401(k), 403(b), and most 457(b) employee contribution limit is $24,500. If you're 50 or older, you can add a catch-up contribution of up to $8,000. Some plans also allow a higher "super catch-up" of $11,250 for ages 60 through 63, but only if your employer's plan has adopted that feature.

Two practical points. First, payroll contributions can only come out of paychecks you haven't received yet, so if you want to change your deferral rate, the window closes sooner than December 31. Second, certain higher-paid employees are now required to make their catch-up contributions on a Roth (after-tax) basis, so it's worth checking how your plan handles that.

Traditional and Roth IRA contributions follow a different timeline. The 2026 limit is $7,500, plus a $1,100 catch-up if you're 50 or older, and you generally have until the tax filing deadline to make them.

2. Look at Your HSA

If you're covered by a qualifying high-deductible health plan, the 2026 HSA limits are $4,400 for self-only coverage and $8,750 for family coverage, with an extra $1,000 catch-up once you're 55. Many people treat an HSA as a spending account. Some use it as a long-term tax-advantaged way to set money aside for future healthcare costs, which are a significant part of most retirement plans.

One timing note: HSA contributions generally stop once you enroll in Medicare, so if you're approaching 65, check your dates. We covered how Medicare enrollment fits into a retirement plan in our post on Medicare Open Enrollment. [Medicare Open Enrollment Blog Article]

3. Consider Whether a Roth Conversion Makes Sense This Year

A Roth conversion moves money from a pre-tax account, like a traditional IRA, into a Roth IRA. You pay income tax on the converted amount in the year of conversion, and in exchange, qualified withdrawals from the Roth in the future are generally tax-free and Roth IRAs aren't subject to RMDs during your lifetime.

Whether it makes sense depends heavily on the year. People who have recently retired but haven't started Social Security or RMDs sometimes find themselves in an unusually low-income year, which can be a window to consider converting. A few things interact with a conversion, and they're easy to overlook:

• The converted amount is added to your taxable income for the year, which can push you into a higher bracket.

• Higher income can increase how much of your Social Security benefit is taxable, and can trigger higher Medicare premiums (IRMAA), which look back at your income from two years earlier.

• If you're 65 or older, the temporary $6,000 senior deduction available for tax years 2025 through 2028 begins to phase out once income passes $75,000 for single filers or $150,000 for joint filers, so a conversion can reduce it.

• Conversions generally can't be undone once completed, and they must be finished by December 31 to count for 2026.

This is one where we model a few scenarios with a client's actual numbers rather than relying on a rule of thumb.

For Retirees

4. Confirm Your Required Minimum Distribution

If you're subject to RMDs, you generally need to take them by December 31 each year. The starting age is 73 if you were born between 1951 and 1959, and 75 if you were born in 1960 or later. Your very first RMD can be delayed until April 1 of the following year, but that means taking two distributions in the same tax year, which can create a larger tax bill than expected.

The penalty for missing an RMD is steep: a 25% excise tax on the amount you should have withdrawn, which may be reduced to 10% if corrected promptly. If you have multiple retirement accounts, the calculation and where you can take the money from can vary by account type, so it's worth confirming rather than assuming.

5. Consider a Qualified Charitable Distribution

If you're 70½ or older and give to charity, a QCD lets you send money directly from your IRA to a qualified charity. The amount isn't counted as taxable income, and it can count toward your RMD. For 2026, the annual limit is $111,000 per person.

A few rules matter here. The money has to go directly from the IRA to the charity, not through you first. QCDs generally can't be made to donor-advised funds or private foundations. And because a QCD lowers your adjusted gross income instead of acting as an itemized deduction, it can also help with income-sensitive items like the senior deduction and Medicare premium brackets. Keep your receipts and make sure your tax preparer knows about the QCD, because the custodian's tax form generally won't identify it as a QCD.

6. Review Your Taxable Accounts and Your Withholding

Two quick checks round out the list.

Taxable investment accounts. If you hold investments outside of retirement accounts, year-end is a natural time to look at realized gains and losses. Some people use losses to offset gains, a practice often called tax-loss harvesting. Be aware of the wash-sale rule, which can disallow a loss if you buy the same or a substantially identical investment within 30 days before or after the sale. Trading decisions should always be driven by your overall plan, not the tax calendar alone.

Withholding and estimated payments. If you've taken larger-than-usual IRA withdrawals, converted to a Roth, or realized gains, check whether your withholding or estimated tax payments are keeping pace. Underpayment can lead to penalties, and the final estimated tax payment for 2026 is due in mid-January 2027. A quick conversation with your tax professional in November is a lot easier than an unpleasant surprise in April.

A Note on State Taxes

Indiana and Illinois treat retirement income differently, and many of our clients have connections to both. It's worth confirming how your state handles IRA distributions, Roth conversions, and pension income before making year-end decisions.

Putting It Together

None of these items works in isolation. A Roth conversion affects Medicare premiums. A QCD affects your adjusted gross income, which affects the senior deduction. An RMD affects your bracket, which affects the conversion you might have considered. That's the reason we prefer to look at them together, with your actual numbers, in a single conversation before the year ends, and to coordinate with your CPA so everyone is working from the same picture.

The IRS typically announces the following year's contribution limits in the fall, so we'll also be watching for 2027 numbers as they're released.

Frequently Asked Questions

What is the deadline for year-end tax moves in 2026? For most items, including Roth conversions, RMDs, and QCDs, the deadline is December 31, 2026. IRA and HSA contributions for 2026 can generally be made until the tax filing deadline in 2027, while payroll-based 401(k) contributions depend on your employer's last paycheck of the year.

How much can I contribute to a 401(k) in 2026? The employee contribution limit is $24,500. Those 50 and older can add a catch-up of $8,000, and some plans allow an increased catch-up of $11,250 for ages 60 through 63.

Do I have to take a required minimum distribution this year? It depends on your age and account type. The RMD starting age is 73 for those born between 1951 and 1959 and 75 for those born in 1960 or later. Roth IRAs don't require RMDs during the owner's lifetime.

What is a qualified charitable distribution (QCD)? A QCD is a direct transfer from an IRA to a qualified charity by someone age 70½ or older. It generally isn't included in taxable income and can count toward the year's RMD, up to $111,000 per person in 2026.

Is a Roth conversion a good idea before the end of the year? It depends on your income, tax bracket, Medicare premium thresholds, and other factors. A conversion adds to your taxable income for the year and generally can't be reversed, so it's best evaluated with your actual numbers before December 31.

Let's Talk Through Your Year-End Review

If you're in Northwest Indiana or the Greater Chicagoland area and would like help sorting out which of these items apply to you before the year ends, we'd welcome the conversation. We'll go through your accounts, your timeline, and how the pieces fit together, and we work alongside your CPA when that's helpful.

Schedule a time to talk with Aaron →

This article is for general informational and educational purposes only and does not constitute personalized investment, tax, or legal advice. Tax laws and contribution limits are subject to change, and individual circumstances vary. Please consult a qualified tax professional or attorney regarding your specific situation.

Investment advisory services offered through Redhawk Wealth Advisors, Inc., an SEC-Registered Investment Advisor. SEC registration does not imply any level of skill or understanding. Redhawk Wealth Advisors and Patten Financial Group are unaffiliated and separate legal entities.