Before the holiday calendar fills up, make room for one more conversation: Am I missing opportunities to lower this year’s tax bill?
You don’t need every tax document in hand to start. Gather your latest pay statements, investment activity, retirement contributions and planned charitable gifts, then ask your tax professional which decisions deserve attention now. Some opportunities require action before December 31; others, including eligible IRA and HSA contributions, may remain available into the following year.
The goal is a coordinated plan—not a last-minute scramble or spending money simply to get a deduction.
1. Put investment losses to work thoughtfully
If an investment in a taxable account has lost value, selling it may create a capital loss that can offset capital gains. If losses exceed gains, married couples and single individuals are limited to deducting a maximum of $3,000 of the excess every year. $1,500 if filing married filing sperate. Unused losses can carry forward to later years. See IRS Topic 409, Capital Gains and Losses.
Watch the wash-sale rule: buying substantially identical stock or securities within 30 days before or after a loss sale can disallow the deduction. The IRS illustrates this in its wash-sale guidance. Before selling, ask your tax professional and financial planner to review the tax impact alongside your investment goals.
Ask before year-end: Do my realized gains, available losses and prior-year loss carryforwards suggest any trades worth considering?
2. Review when income and deductions will count
Timing can affect which year income and expenses appear on your return. Under the cash method, income is generally reported when constructively received and expenses are generally deducted when paid, subject to applicable rules. The accrual method works differently. See IRS Publication 538, Accounting Periods and Methods.
Ask your tax professional to compare this year’s expected income and deductions with next year’s before accelerating a payment or discussing a permissible change in income timing. Do not assume you can move income into January simply because you prefer next year’s tax treatment, or that paying an expense early automatically makes it deductible.
Ask before year-end: Would changing the timing of an otherwise planned transaction help my overall tax picture, and what rules apply?
3. Make charitable giving intentional
If giving is already part of your year-end plans, consider the tax rules before choosing the amount, asset or timing. Beginning in 2026, eligible married couples who do not itemize may deduct up to $2,000 of qualifying cash gifts, or $1,000 if filing single. Noncash gifts & gifts to donor-advised funds do not qualify for this particular deduction. See IRS Publication 6196, Charitable Contribution Deduction Tips for Non-Itemizers.
For taxpayers who itemize, a new 2026 floor generally allows a charitable deduction only for contributions exceeding 0.5% of adjusted gross income, with additional limitations potentially applying. That makes it worth discussing whether to combine planned gifts into one year or donate appreciated investments rather than cash. If the taxpayer itemizes, they lose the benefit of the $2,000 ($1,000 if single) deduction, regardless of if their charitable deduction is limited by the 0.5% floor.
Confirm the recipient qualifies and keep the required records. A gift of $250 or more generally requires a contemporaneous written acknowledgment from the charity. See IRS Topic 506, Charitable Contributions.
Ask before year-end: How should I complete my planned gifts, and what documentation should I obtain?
4. Check your retirement contribution room
Start by reviewing what you have contributed through payroll and whether increasing your contributions fits your budget. For 2026, the employee contribution limit for 401(k) plans is $24,500, with additional catch-up contributions available to eligible older participants. If you’re age 50 or older, ask your tax professional which catch-up provisions apply to your 401(k) and IRA, and how your salary affects the applicable rules. Some catch-up contributions may not be deductible.
Traditional IRA deductibility depends on factors including income and workplace retirement-plan coverage. See the IRS announcement of 2026 retirement contribution limits.
Not every retirement contribution lowers today’s tax bill. Traditional retirement contributions may offer a current tax benefit; Roth IRA contributions are made with after-tax dollars and do not generate a deduction. For workplace plans, check remaining payroll dates and plan-specific requirements now rather than assuming an IRA deadline applies. Eligible taxpayers generally have until April 15, 2027, to make 2026 traditional or Roth IRA contributions. See Fidelity’s 2026 IRA contribution deadline guide.
Ask before year-end: Should I adjust remaining payroll contributions, and would a deductible IRA contribution fit my situation?
5. Revisit your health savings account (HSA)
If you are eligible to contribute to a health savings account, check whether you have unused contribution room. The 2026 base limits are $4,400 for self-only coverage and $8,750 for family coverage under IRS Revenue Procedure 2025-19.
HSA contributions made outside pre-tax payroll may qualify for a federal income tax deduction. Contributions through payroll and from your employer must also be included when reviewing your limit, and eligibility matters—especially if your health coverage changed or you enrolled in Medicare. Eligible taxpayers generally have until April 15, 2027, to make 2026 contributions. See IRS Publication 969, Health Savings Accounts and Other Tax-Favored Health Plans.
Ask before year-end: Am I eligible for additional contributions, and how much room remains after all funding sources are counted?
Start with a conversation
You do not need to pursue every strategy. Bring your tax professional a current snapshot and ask which actions fit your circumstances, which require completion before December 31, and which can wait until the contribution deadline. Coordinate any investment decisions with your financial planner.
A thoughtful review can help you identify opportunities without letting taxes drive decisions that do not otherwise make sense. Start now so there is time to ask questions, confirm the rules and act deliberately.
This article provides general educational information about federal taxes based on sources reviewed November 6, 2026. It is not individualized tax, legal or investment advice. Eligibility, limitations, state tax treatment and deadlines vary. Consult your tax and financial professionals before taking action.
