4 strategies for an organized U.S. tax season, from Morningstar

Benz, director of personal finance and retirement planning for Morningstar and co-host of The Long View podcast, lays out four steps designed to keep people from scrambling for documents as the tax deadline approaches. The overall theme is preparation: assembling information early, understanding which deductions might apply, and lining up retirement-account contributions so they can be reflected when a return is filed.

Her first strategy focuses on keeping tax records organized through a checklist or organizer, whether taxpayers prepare on their own or work with an accountant. She notes that tax organizers often arrive as paper or digital forms that can include prepopulated tax data from the prior year, helping people track changes in income, interest earned on investments, and charitable giving across tax seasons.

The second strategy centers on the choice between itemizing deductions and taking the standard deduction. Benz writes that if a taxpayer uses an advisor, the advisor may already provide guidance based on the 2024 return. For people preparing their own returns, she recommends assessing the major deductible items first and comparing them with the standard deduction.

For the 2025 tax year, Benz says itemizing could be worthwhile if deductible expenses exceed the standard deduction of $15,750 for single taxpayers and $31,500 for married couples filing jointly. She also describes a senior deduction of $6,000 available to people over 65 for both itemizers and non-itemizers, with a $12,000 amount for married couples filing jointly if both partners are over 65, while noting that this deduction phases out for modified adjusted gross incomes above $75,000 for singles and above the double amount for married couples filing jointly.

Benz also points taxpayers toward common large-ticket deductions, including state and local taxes (such as property taxes), home mortgage interest, and medical expenditures exceeding 7.5% of adjusted gross income. She adds that the maximum deductible amount for the state and local tax deduction increased from $10,000 to $40,000 after a tax and domestic policy bill passed last year, and she says the higher amount phases out for modified adjusted gross incomes above $500,000, while people with MAGI above $600,000 face a $10,000 cap on deductible state and local taxes.

If taxpayers decide to itemize, Benz recommends rounding up supporting documentation for the deductible expenses. She says if receipts are missing, credit card statements from the previous year can help identify those expenses, and she notes that healthcare providers and pharmacies are often willing to provide a year-end statement documenting out-of-pocket costs.

Her third strategy is to round up investment documentation, beginning with the W-2s and 1099s that report different types of income. Benz says investment firms often provide “tax centers” where people can download or print the relevant forms, and she suggests reviewing 1099s for information that could affect taxes and tax planning decisions.

As part of that review, Benz points to situations involving capital gains taxes, writing that if someone owes significant capital gains taxes but hasn’t sold anything, that can be a “red flag.” She links that concern to reviewing asset location and mentions using tax-efficient assets such as equity exchange-traded funds in a taxable brokerage account.

Benz’s fourth strategy is to make IRA and health savings account contributions as soon as possible, emphasizing that deadlines for contributing to an IRA or an HSA are aligned with the tax-filing deadline. She says that if taxpayers want to deduct contributions on their return, they generally need to make the contributions before filing, and she adds that this also applies for the Saver’s Credit.

In her guidance, Benz also explains eligibility constraints. She says IRA contributions require earned income and that HSA contributions require coverage by a qualifying high-deductible healthcare plan, while noting that an HSA is off-limits if someone is covered by Medicare. She also says contributions can be made whether someone itemizes or not, but the timing matters if the taxpayer expects the deduction to appear on the filed return.

For the 2026 tax year, Benz provides a practical “how much to put in each month” approach for IRA contributions. She says investors under age 50 can reach a full $7,500 maximum IRA contribution by putting in $625 a month, while investors over 50 can max out with a $716 monthly contribution.

Benz’s advice comes through an article provided to The Associated Press by Morningstar. Morningstar also directs readers to its personal finance page for more tax-planning and IRA resources for 2026, including a link to Morningstar’s tax-planning and IRA resources for 2026.

And while this story focuses on preparation steps rather than the filing deadline itself, MSI previously reported coverage of the 2026 IRS filing deadline and extension option here, which can be useful for mapping these planning steps to the calendar.