Quick Answer: Most year-end tax moves have to be completed by December 31, 2026. That includes required minimum distributions (RMDs), Roth conversions, tax-loss harvesting, and 401(k) payroll deferrals. A few items, like IRA and HSA contributions, can wait until the April 2027 filing deadline. For retirees, pre-retirees, business owners, and executives, the next seven weeks are the last chance to shape this year's tax picture. Every decision should be coordinated with your tax professional.
Every November, our firm starts having the same conversation with clients across Northwest Indiana and Greater Chicagoland: "What do we still need to do before the year ends?"
It's the right question. Many of the most effective tax planning opportunities run on a calendar-year clock. Once December 31 passes, they're gone, and there's no going back to fix them when you file in the spring.
This checklist is organized by life stage, so you can go straight to the sections that apply to you. Many families will find something useful in more than one.
Key Year-End Deadlines at a Glance
For Retirees: RMDs, Capital Gains, and the New Senior Deduction
Confirm your RMDs are complete. If you're 73 or older, your required minimum distributions from traditional IRAs and 401(k)s generally must be taken by December 31. Missing one can trigger a 25% excise tax on the amount not withdrawn. That penalty may be reduced if the shortfall is corrected promptly, but it's far better to avoid it. If you inherited an IRA, review whether annual distributions are required as well. The rules for inherited accounts have changed in recent years and catch many families off guard.
Look at the 0% capital gains bracket. Retirees with modest taxable income may be able to realize long-term gains at a 0% federal rate. For 2026, the 0% long-term capital gains bracket applies to taxable income up to $49,450 for single filers and $98,900 for married couples filing jointly. Realizing gains within that range, sometimes called tax-gain harvesting, can reset your cost basis for the future. Keep in mind that long-term gains stack on top of ordinary income when measured against the threshold, so selling too much pushes the excess into the 15% rate.
Account for the new senior deduction. Under the One Big Beautiful Bill Act, each taxpayer age 65 or older can claim an extra $6,000 deduction ($12,000 if both spouses qualify) on top of the existing additional standard deduction. The catch is that it phases out at MAGI of $75,000 for single filers and $150,000 for married couples filing jointly. Any year-end move that increases income, such as a Roth conversion or a large capital gain, should be measured against that phase-out.
For Pre-Retirees: Roth Conversions and Maximizing Contributions
Evaluate a Roth conversion before December 31. The years between retirement and the start of RMDs and Social Security are often a lower-income window, which can make Roth conversions worth considering. A conversion must be completed by year-end to count for 2026. Two cautions apply. First, conversions add to taxable income and can push you into a higher bracket. Second, Medicare uses a two-year lookback for IRMAA surcharges, so income you recognize in 2026 can affect your Medicare premiums in 2028. Running the numbers before converting matters more than the conversion itself.
Finish your 401(k) contributions through payroll. The 2026 employee deferral limit is $24,500, plus an $8,000 catch-up for those 50 and older and an $11,250 "super catch-up" for ages 60–63. Unlike IRAs, workplace plan contributions must come through payroll by your final 2026 paycheck. If you're behind, there may still be time to raise your deferral percentage for December.
Know the new Roth catch-up rule. Starting this year, employees aged 50 or older who earned more than $150,000 in FICA wages from their employer in the previous year must make all catch-up contributions on a Roth (after-tax) basis. It's worth confirming with your payroll department that your catch-up dollars are being handled correctly.
Use your FSA balance. Flexible spending account dollars are often use-it-or-lose-it. Check your plan's grace period or carryover rules before the year ends.
For Business Owners: Entity, Retirement Plan, and Deduction Timing
Review your retirement plan options now. Some plan types must be in place by December 31 to accept certain contributions for the current year, while others can be established up to the tax filing deadline. If you've been considering a Solo 401(k), SEP IRA, or cash balance plan, year-end is the time to decide which deadlines apply to you.
Revisit the SALT deduction. The state and local tax deduction cap was raised under recent legislation, but it phases down at higher incomes. The $500,000 phase-out threshold increases 1% each year, so it is $505,000 for 2026. Many states also offer a pass-through entity tax election that may help business owners work around the cap. Talk with your CPA about whether it makes sense for your entity.
Coordinate income and expense timing. Depending on your entity type and accounting method, there may be flexibility in when you recognize income or pay expenses. These decisions belong with your CPA, but they work best when your financial advisor and tax professional are looking at the same numbers.
Check your buy-sell and succession documents. Year-end is a natural checkpoint to confirm your buy-sell agreement still reflects your business's current value and that any funding behind it is adequate. https://www.pattenfinancial.com/pfg-blog/week-4-funding-strategies-for-buy-sell-agreements
For Corporate Executives: Elections and Equity Compensation
Make your deferred compensation elections. Nonqualified deferred compensation elections for next year's pay generally must be made before that year begins. If your employer offers a plan, review your 2027 election before your enrollment window closes. https://www.pattenfinancial.com/pfg-blog/understanding-executive-bonus-plans-a-tool-for-rewarding-key-talent
Check withholding on equity compensation. RSU vesting and bonuses are often withheld at a flat supplemental rate, which may not match your actual bracket. If you had a large vesting event this year, review whether your withholding and estimated payments cover what you'll owe in April.
Complete open enrollment carefully. If you're eligible for an HSA, the 2027 limits are already set at $4,500 for self-only coverage and $9,000 for family coverage. That's worth factoring into your health plan election.
For Everyone: Harvesting Losses, Gifting, and Beneficiaries
Consider tax-loss harvesting. Selling investments at a loss in taxable accounts can offset realized gains. Net capital losses can reduce ordinary income by up to $3,000 a year, and the rest carries forward. Be mindful of the wash-sale rule, which disallows the loss if you buy a substantially identical investment within 30 days before or after the sale.
Make annual exclusion gifts. If you plan to give to children or grandchildren, gifts within the annual exclusion amount ($19,000 per recipient for 2026) generally don't require a gift tax return. Unused exclusions don't carry forward to next year.
Review beneficiary designations. Retirement accounts and life insurance pass by beneficiary designation, not by your will. A marriage, divorce, birth, or death in the family this year is a reason to confirm every designation is current. PFG estate planning article
Year-End Review Checklist
Use these questions to guide your conversation with your advisor and tax professional:
Have all required minimum distributions, including from inherited accounts, been taken for 2026?
Is there room to realize long-term gains in the 0% capital gains bracket?
Would a Roth conversion make sense this year, after accounting for IRMAA and the senior deduction phase-out?
Am I on track to reach my 401(k) contribution goal by my final paycheck?
If I'm 50 or older and a higher earner, are my catch-up contributions being handled as Roth?
Are there losses in my taxable accounts that could offset gains?
Have I made my deferred compensation and open enrollment elections for 2027?
Are my beneficiary designations up to date?
Will my withholding and estimated payments cover my 2026 tax bill?
Frequently Asked Questions
What is the deadline for year-end tax planning moves in 2026?
Most moves, including RMDs, Roth conversions, tax-loss harvesting trades, and annual exclusion gifts, must be completed by December 31, 2026. IRA and HSA contributions for 2026 can be made until April 15, 2027.
Can I still contribute to my 401(k) for 2026 after December 31?
Generally, no. Employee 401(k) deferrals must be made through payroll by your final paycheck of the year. IRA contributions are different and can be made until the filing deadline.
What happens if I miss my RMD?
A missed RMD can trigger a 25% excise tax on the amount not withdrawn. That may be reduced to 10% if the shortfall is corrected in a timely manner. Contact your custodian and tax professional as soon as possible if you've missed one.
Does a Roth conversion affect my Medicare premiums?
It can. Medicare's IRMAA surcharges are based on your income from two years prior, so a 2026 conversion could raise your 2028 Part B and Part D premiums.
Who is affected by the new Roth catch-up rule?
Workers age 50 and older whose prior-year FICA wages from their employer exceeded $150,000 must make 401(k) catch-up contributions as Roth contributions starting in 2026.
Plan Before the Clock Runs Out
Year-end planning works best when your investment strategy, tax picture, and long-term goals are all part of the same conversation. Our firm works with families, business owners, and executives throughout Northwest Indiana and Greater Chicagoland to review these decisions before December 31, in coordination with their CPA or tax professional.
Schedule a complimentary year-end review with Aaron Patten
Planning for income beyond this tax year? Download our complimentary eBook, A Guide to Retirement Income Planning: Strategies for Sustainable Income, to see how tax-aware withdrawal strategies fit into a sustainable retirement income plan.
This article is for educational purposes only and should not be considered tax, legal, or investment advice. Tax laws are complex and subject to change. Please consult your tax professional before making decisions based on this information.
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.
