Tax Planning Strategies: 11 Tax Moves to Check Before Year-End

Tax planning means making an informed choice before a tax result is locked in. Tax filing means reporting what already happened.

The best tax planning strategies are not secret deductions. Personal tax planning is a set of timely checks: withholding, estimated payments, gains and losses, the wash-sale rule, a Roth conversion, retirement and HSA contributions, charitable gifts, credits, required distributions, and clean records.

Use the 11 checks below for year-end tax planning. The right move depends on the tax year, filing status, state, income, account type, and the next several years, not just this year's bill.

Start with what is still open. Some moves must happen by year-end. Some can wait until the tax-return due date. Some must run through payroll. Each rule has its own clock. Check that clock before you act.

1. Check federal withholding

Compare expected tax with what has already been withheld.

The IRS Tax Withholding Estimator can help employees update Form W-4 after a marriage, divorce, second job, large raise, investment income change, or other major event. A refund is not always proof that withholding was correct. A balance due is not always proof that it was wrong.

2. Check estimated taxes

Income without enough withholding may require estimated payments. Common examples include self-employment, interest, dividends, rent, capital gains, and some retirement distributions.

IRS Publication 505 explains withholding and estimated-tax rules. Form 1040-ES provides worksheets. State rules can differ.

3. Review realized and unrealized gains

List sales already made and positions you may sell. Separate short-term from long-term holdings because federal rates can differ.

Do not sell a good investment only to create a tax result. Tax is one input. Risk, diversification, cash needs, and the investment case still matter.

4. Use tax-loss harvesting carefully

Tax-loss harvesting means selling an investment below its tax basis so the realized loss may offset capital gains and, within federal limits, some other income.

The move can help when:

the investment no longer fits;

a diversified replacement can keep the portfolio on plan;

trading cost and spread are small; and

the wash-sale rule is controlled.

It can hurt when it increases concentration, creates a wash sale, raises state tax, or swaps into something you do not want.

5. Understand the wash-sale rule

The wash-sale rule can disallow a loss when you buy substantially identical stock or securities within the 61-day window that starts 30 days before the loss sale and ends 30 days after it.

The rule can also matter when a spouse or an IRA or Roth IRA buys the replacement. An IRA-related wash sale can be especially costly because the disallowed loss may not simply raise taxable-account basis.

The federal wash-sale window is explained in IRS Publication 550. "Substantially identical" is a facts-and-circumstances test.

6. Model a Roth conversion

A Roth conversion moves pre-tax retirement money into a Roth account. The taxable amount generally enters income in the conversion year.

Retirement tax planning may include a conversion when the current marginal rate is expected to be lower than a later rate, when future required distributions are a concern, or when estate goals favor Roth assets. It may be a poor fit when the added income raises another tax, premium, credit phaseout, or cash problem.

Before converting, model:

federal and state marginal rates;

Medicare income-related premiums when relevant;

Affordable Care Act credit effects;

capital-gain and deduction interactions;

cash available to pay tax;

the time before the money is needed; and

the possibility that future law or income is different.

A Roth conversion is a multi-year tax decision, not an automatic year-end move. See Form 8606 instructions and the full Roth IRA guide.

7. Check retirement and HSA contribution opportunities

For 2026, the employee 401(k), 403(b), and most governmental 457 plan deferral limit is $24,500. The IRA contribution limit is $7,500. Separate catch-up rules apply.

Deadlines are not all the same:

workplace salary deferrals generally must come through payroll during the year;

IRA contributions can generally be made by the tax-return due date, without extensions, for the prior year;

HSA timing follows its own rules; and

employer and self-employed plan contributions can have different deadlines.

Use the rule for the exact account. The 401(k) contribution limit guide and HSA investment guide explain the 2026 details.

8. Confirm required minimum distributions

Missing a required minimum distribution, or RMD, can create an excise tax and a correction process. Check:

which accounts require a distribution;

the owner's age and required beginning date;

inherited-account rules;

amounts already taken; and

whether a workplace-plan exception applies.

Roth IRA owners do not have lifetime RMDs. Beneficiaries follow separate rules.

9. Plan charitable gifts before the deadline

The method can matter as much as the amount.

Depending on eligibility and goals, compare:

a cash gift;

appreciated property;

a donor-advised fund;

a qualified charitable distribution from an IRA; and

bunching gifts into one year.

Substantiation rules apply. A gift that does not qualify or lacks required records may not produce the expected deduction.

10. Check deductions and credits you can still affect

A deduction reduces taxable income. A credit reduces tax, subject to its rules. A deferral moves a tax event to another period.

Review the items that fit your facts, such as education, dependent care, energy improvements, business purchases, health coverage, or retirement saving. Do not assume a social-media list applies to your filing status or income.

11. Keep the records that prove the result

Save:

basis and purchase records;

trade confirmations;

charitable acknowledgments;

estimated-tax confirmations;

retirement and HSA contribution records;

conversion and distribution forms;

business receipts and mileage records; and

the assumptions behind a major choice.

Tax planning is only as strong as the return and records that support it.

A planning calendar, not a filing deadline chart. Confirm the exact tax-year deadline with the IRS filing resources and the account provider.

Common questions

Is tax-loss harvesting always worth it?

No. It should improve the after-tax portfolio without weakening the investment plan. A small loss may not justify trading cost, spread, complexity, or a poor replacement.

How long do I wait to avoid a wash sale?

The federal rule looks at 30 days before and 30 days after the loss sale. Waiting more than 30 days after the sale can address the forward part, but you must also check purchases made before the sale and activity in related accounts.

Is a Roth conversion tax-free?

Usually not. Pre-tax amounts converted to Roth generally count as taxable income. Nondeductible basis can reduce the taxable share, and Form 8606 plus the aggregation rule matter.

What is strategic tax planning?

Strategic tax planning compares the current choice with future years and other goals. It may coordinate income, gains, retirement accounts, charitable gifts, business decisions, and estate plans instead of minimizing one year's tax at any cost.

When should I use a tax professional?

Get qualified help for a large conversion, business sale, divorce, stock compensation, multistate income, estate or trust, foreign reporting, tax debt, or any move you do not fully understand.

This guide is general federal tax education, not tax, legal, or investment advice. Tax laws, inflation adjustments, forms, and deadlines change. Verify the current rule and state treatment before acting.

Sources

Internal Revenue Service, Publication 550: Investment Income and Expenses. Accessed July 30, 2026.

Internal Revenue Service, Tax Withholding Estimator. Accessed July 30, 2026.

Internal Revenue Service, tax withholding. Accessed July 30, 2026.

Internal Revenue Service, Publication 505: Tax Withholding and Estimated Tax. Accessed July 30, 2026.

Internal Revenue Service, Form 1040-ES. Accessed July 30, 2026.

Internal Revenue Service, Instructions for Form 8949. Accessed July 30, 2026.

Internal Revenue Service, Instructions for Form 8606. Accessed July 30, 2026.

Internal Revenue Service, 2026 retirement contribution limits. Accessed July 30, 2026.

Internal Revenue Service, required minimum distributions. Accessed July 30, 2026.

Internal Revenue Service, charitable contribution deductions. Accessed July 30, 2026.

Internal Revenue Service, Topic 309: Roth IRA contributions. Accessed July 30, 2026.

Internal Revenue Service, filing resources. Accessed July 30, 2026.