Year-End Tax Moves for Individuals: Checklist and Deadlines

Quick overview

This checklist explains the common, high-impact year-end tax moves individuals should review and the deadlines that typically apply. I’ve used these strategies with clients over 15+ years to tighten tax outcomes before year-end. The goal here is practical: reduce your tax bill (or avoid surprises) without taking on undue risk.

Note: This is educational information, not individualized tax advice. Always confirm deadlines and plan rules with your tax advisor and the IRS (see links below).

How year-end timing matters

Many tax benefits are tied to the calendar year. For employer plans (401(k), 403(b), etc.), contributions are tied to pay-period deferrals and generally must be made by December 31 to count for that tax year. IRA contributions, however, can usually be made up to the federal tax filing deadline (typically April 15 of the following year) for the prior tax year (see IRS Publication 590-A). Charitable gifts generally must be completed by December 31 to qualify for that year’s deduction.

For timelines and IRS guidance, see the IRS site on retirement and IRA rules (irs.gov) and the IRS page on charitable contributions (irs.gov/charities). The Consumer Financial Protection Bureau also offers practical guidance on retirement saving decisions and avoiding scams (consumerfinance.gov).

High-priority year-end moves (checklist with deadlines and quick notes)

1. Maximize employer retirement plan contributions (deadline: December 31)

• Why: Reduces taxable wages for the year and can lower AGI, which affects itemized deductions and credits.
• Action: Increase your 401(k) deferral via payroll before the final pay period of the year. Check with HR or your plan administrator for any payroll cutoffs.
• See also: Understanding Employer Match: How to Maximize Free Retirement Money (FinHelp) for tips on not leaving match behind: https://finhelp.io/glossary/understanding-employer-match-how-to-maximize-free-retirement-money/

1. Fund or recharacterize IRAs (deadline: tax-filing deadline, usually April 15)

• Why: IRA contributions can lower taxable income (traditional IRA) or grow tax-free (Roth IRA). You have until the filing deadline to contribute to the prior tax year.
• Action: If eligible for a deductible IRA contribution, fund before the filing deadline or consider a backdoor Roth if income limits block direct Roth contributions.
• Source: IRS Publication 590-A (IRAs) explains contribution deadlines and rules.

1. Make charitable contributions (deadline: December 31 for cash gifts)

• Why: Itemized taxpayers can deduct gifts to qualified charities. If you’re over 70½ (rules changed under recent legislation), consider a Qualified Charitable Distribution (QCD) from an IRA to reduce taxable income.
• Action: Donate by Dec 31 and get written acknowledgment for gifts over $250. For non-cash gifts (stock), transfer the asset to the charity before year-end to claim the deduction and avoid paying capital gains.
• Source: IRS Publication 526; consider timing rules and documentation requirements on irs.gov.

1. Tax-loss harvesting (deadline: December 31 execution)

• Why: Selling investments at a loss can offset capital gains and up to $3,000 ($1,500 married filing separately) of ordinary income per year, with excess losses carried forward.
• Action: Harvest losses before year-end, but watch the wash-sale rule: you cannot buy a substantially identical security within 30 days before or after the sale (see IRS wash-sale rules).
• Practical tip: If you want to stay invested, buy a similar (but not substantially identical) ETF or mutual fund to maintain market exposure.

1. Adjust withholding and estimated tax payments (timing: as soon as your income forecast changes)

• Why: Underwithholding or missed estimated payments can trigger penalties. Reviewing your W-4 and Q4 estimated taxes helps avoid underpayment.
• Action: Update your W-4 with your employer if your expected income, filing status, or credits changed. If you’re self-employed, make timely estimated tax payments—missing payment deadlines can increase penalties.
• Source: IRS pages on withholding and estimated taxes for individuals.

1. Review capital transactions and year-end sales

• Why: Realized gains and losses are taxed in the year they occur. If you expect large gains, consider timing sales to the following tax year or offset with harvested losses.
• Action: Coordinate with your broker to confirm settlement dates and make trades early enough to effect the desired tax year.

1. Consider Roth conversions strategically (deadline: December 31 to count for a tax year)

• Why: Converting traditional IRA assets to a Roth triggers taxable income now but allows future tax-free growth. Doing a partial conversion in a low-income year can be tax-efficient.
• Action: Run a tax projection before a conversion and consider spreading conversions across years to avoid pushing you into a higher tax bracket.

1. Check required minimum distributions (RMDs) and retirement distributions

• Why: Missing an RMD can result in substantial penalties. Also, RMDs increase taxable income and may impact Medicare premiums.
• Action: If you’re subject to RMDs, confirm your plan’s distribution schedule and complete any required withdrawals before the RMD deadline.
• Related: See RMD Strategies and Timing: Reducing Taxes on Required Withdrawals (FinHelp) for distribution tactics: https://finhelp.io/glossary/rmd-strategies-and-timing-reducing-taxes-on-required-withdrawals/

1. Review life changes and tax credits (no single deadline, but plan early)

• Why: Marriage, divorce, birth/adoption, education expenses, or caring for dependent relatives can change credits and deductions.
• Action: Update dependents on payroll and explore credits (Child Tax Credit, education credits, earned income considerations), and collect supporting documents.

1. Verify year-end receipts and statements (deadline: December 31 for many items)

• Why: Proper documentation is required to substantiate deductions and credits during an audit.
• Action: Request donation acknowledgments, broker year-end tax forms (1099-B, 1099-DIV), and verify mortgage interest statements (Form 1098) are correct.

Common mistakes I see in practice

• Waiting until after December to plan. Many moves require action before the calendar year closes.
• Confusing IRA vs. employer-plan deadlines (IRAs have extended contribution deadlines; employer plans do not).
• Overlooking wash-sale rules when tax-loss harvesting.
• Assuming a tax preparer will automatically make all adjustments—taxpayers who prepare projections and provide clear documents get better year-end results.

Quick decision framework (use this at year-end)

1. Project your taxable income for the year. 2. Identify whether you’ll itemize or take the standard deduction. 3. Prioritize moves that lower adjusted gross income (retirement deferrals, HSA contributions) and preserve credits. 4. Confirm timing and plan rules. 5. Execute trades or transfers with settlement lead time in mind. 6. Document everything.

Useful resources and internal reads

• IRS retirement account rules (Publication 590-A): https://www.irs.gov/publications/p590a
• IRS charitable contributions guidance: https://www.irs.gov/charities-non-profits/charitable-contributions
• Consumer Financial Protection Bureau on retirement planning: https://www.consumerfinance.gov
• Internal FinHelp articles:
• Understanding Employer Match: How to Maximize Free Retirement Money — https://finhelp.io/glossary/understanding-employer-match-how-to-maximize-free-retirement-money/
• RMD Strategies and Timing: Reducing Taxes on Required Withdrawals — https://finhelp.io/glossary/rmd-strategies-and-timing-reducing-taxes-on-required-withdrawals/
• Essential Tax Deadlines Every Individual Should Know — https://finhelp.io/glossary/essential-tax-deadlines-every-individual-should-know/

Final takeaways

Year-end tax moves are a mix of timing, documentation, and deliberate choices about when you recognize income and expenses. In my practice, clients who run a simple year-end projection and act on the top one or two levers (retirement deferrals, charitable timing, or loss harvesting) typically see the best balance of tax savings versus complexity.

If you’re unsure which moves fit your situation, consult a CPA or tax advisor who can review your projections and plan rules. For general IRS guidance, start at irs.gov and confirm any deadlines tied to employer plans with your HR department.

Disclaimer: This article is educational and not individualized tax advice. Tax law changes frequently—confirm current rules and limits with the IRS or a qualified tax professional.