This list is short on purpose.
December is the month you have the least room for anything extra, so here are twelve year-end planning items worth checking now. Some have December 31 tax deadlines. Others require earlier payroll, custodian, state, or plan-specific action.
At the bottom are three deadlines that generally fall in 2027. Knowing which decisions can wait—and which cannot—is half the battle.
The List
401(k) deferrals: Review your remaining payroll opportunities against the 2026 employee deferral limit: $24,500, or $32,500 if you are 50 or older, with a higher total of $35,750 if you turn 60 through 63 during the year. These amounts assume your plan permits catch-up contributions and you have sufficient eligible compensation. Coordinate payroll changes before your employer’s cutoff; self-employed arrangements can have different timing rules.
Roth catch-up check: If your 2025 Social Security wages from the employer sponsoring your plan exceeded $150,000, confirm that your 2026 catch-up contributions are being treated as Roth contributions. This requirement applies to catch-up contributions, not your entire employee deferral.
Plan design changes: If you are considering a cash-balance plan or changes to an existing retirement plan, have your plan administrator and actuary identify any year-end amendment, notice, or operational deadlines. Some changes can be made later; others require action before year-end or before benefits accrue.
Withholding: Review your final payroll opportunities if your 2026 income came in higher than planned. Federal income tax withholding is generally treated as paid evenly throughout the year, so additional year-end withholding may help address earlier underpayments. A January estimated payment generally does not fix an underpayment from an earlier installment period.
Required minimum distributions: If you are subject to a 2026 RMD, generally take it by December 31. A first age-based RMD can generally wait until April 1, 2027, but that may put two RMDs in 2027. Lifetime Roth accounts are exempt; certain current-employer plans offer a still-working exception, and inherited accounts follow separate rules.
Qualified charitable distributions: If you are at least 70½ when the distribution occurs, consider a direct IRA transfer to an eligible charity. The 2026 QCD limit is $111,000 per person. Qualifying amounts are excluded from taxable income and can satisfy an RMD, but donor-advised funds do not qualify. Deductible IRA contributions made at age 70½ or later can reduce the exclusion.
Charitable gifts and donor-advised funds: Start appreciated-stock transfers early enough for the gift to be completed by December 31. A fair-market-value deduction generally requires holding the stock for more than one year, and deductions remain subject to itemization, applicable limits, and documentation. Beginning in 2026, itemizers generally face a charitable deduction floor of 0.5% of adjusted gross income.
Tax-loss harvesting: Execute ordinary stock and fund loss sales by the market close on Thursday, December 31; the trade date generally controls. Avoid purchases of substantially identical securities during the 30 days before and after the sale, including purchases through dividend reinvestment, your IRA, or your spouse’s accounts.
Roth conversions: Complete any conversion intended for the 2026 tax year by December 31, allowing for custodian deadlines. Run the tax projection first: a conversion generally creates taxable income and cannot subsequently be reversed through recharacterization.
Pass-through entity tax: If your practice is an eligible partnership or S corporation, confirm the state election and payment requirements with your CPA. Qualifying entity-level state income tax payments generally produce a federal deduction in the year paid. Do not assume December 31 overrides earlier state election or installment deadlines.
Equipment the practice actually needs: To claim available 100% federal bonus depreciation for 2026, qualifying equipment generally must have been acquired after January 19, 2025, and placed in service by year-end. Eligibility and state treatment vary. Buy for a business reason, not simply for a deduction; the federal 100% allowance does not generally expire after 2026.
Annual exclusion gifts: Complete qualifying present-interest gifts by year-end to use the 2026 annual exclusion of $19,000 per recipient, per donor—or $38,000 combined for two spouses. Unused annual exclusions do not carry forward. Electing gift splitting generally requires Form 709, even when no gift tax is due.
Three Deadlines That Generally Fall in 2027
These often crowd December even though the final deadline comes later. That does not mean the planning can always wait.
Fourth-quarter federal estimated tax payment: January 15, 2027
The final regular federal estimated payment for 2026 is generally due January 15, 2027. Calculate the amount using your full-year projection. Paying in January generally does not eliminate penalties attributable to earlier underpayments, which is why reviewing December withholding can matter.
HSA contributions: April 15, 2027
Eligible individuals can generally make 2026 HSA contributions through April 15, 2027, designating them for 2026. The annual limits are $4,400 for self-only coverage or $8,750 for family coverage, including employer contributions.
An additional $1,000 catch-up may be available at age 55 or older. Eligibility, eligible months, and Medicare enrollment affect the allowable contribution. Each eligible spouse’s catch-up must go into that spouse’s own HSA.
Cash-balance plan adoption and funding: separate deadlines
A new plan can generally be adopted by the employer’s tax-return filing deadline, including extensions. Contributions intended to be deductible for 2026 generally must also meet the applicable return deadline.
Minimum-funding rules operate separately. For a calendar-year plan, the final minimum required contribution for 2026 is generally due September 15, 2027, and quarterly installments may also apply.
Have the actuary and plan administrator confirm the actual deadlines before postponing adoption or funding.
If You Only Have One Hour
Start with payroll. If you are paid twice a month, you ordinarily have about four paychecks between early November and December 31. Deferral and withholding changes must meet your employer’s processing deadlines.
Next, contact custodians about stock gifts, IRA distributions, and Roth conversions. A December 31 tax deadline does not mean an instruction submitted that afternoon will be completed on time.
Then book a conversation with your CPA covering withholding, the pass-through entity tax payment, and any Roth conversion. If retirement-plan design changes are on the table, involve your plan administrator and actuary now.
Use the hour to identify what applies, assign responsibility, and get the time-sensitive work moving—not to assume every item can be completed immediately.
Why a Short List Matters
In the OR, a checklist works only if the critical steps remain easy to find. Your year-end planning list should do the same.
The goal is not to complete all twelve items. It is to identify which ones apply to you, understand their actual deadlines, and avoid letting a time-sensitive decision slip while you are busy with something that can wait.
Building wealth, for me, has always come down to doing the right things on time—and knowing when the rest can wait.
If you looked at this list today, which applicable items could you check off with confidence?
Capably Yours,
Jared
DISCLAIMER
This article is for informational and educational purposes only and does not constitute investment, tax, or legal advice. It does not take into account the specific objectives, financial situation, or needs of any particular person. You should consult your own tax, legal, and investment professionals before acting on any information contained herein. Capable Wealth, a New York registered investment adviser, provides advisory services only where properly licensed or exempt from licensing.