The IRS just announced the 2026 filing season opens January 26, and if you’re treating this like any other year, you’re already behind. The One Big Beautiful Bill Act fundamentally altered how businesses report compensation, how individuals claim deductions, and how the IRS processes returns. CFOs who wait until March to address these changes will spend April firefighting problems that should have been solved in January.
April 15, 2026 remains the deadline for 2025 tax returns. Extensions push that to October 15 for individual and C corporation returns, September 15 for partnerships and S corporations. Those dates are familiar—what’s not familiar is the new reporting infrastructure built around OBBBA provisions.
The IRS will process an estimated 164 million individual returns this year. Most will file electronically, which is no longer optional if you want your refund before summer. The agency is phasing out paper refund checks entirely, forcing taxpayers to use direct deposit or face significant delays.
The new Schedule 1-A handles recently enacted deductions, including no tax on tips, no tax on overtime, no tax on car loan interest, and enhanced deductions for seniors. This isn’t a minor form addition—it’s a structural change in how compensation and deductions are reported.
Businesses that paid significant overtime in 2025 need documentation showing which compensation qualifies for the exclusion. The same applies to tip income—restaurants and hospitality businesses should have separated tip reporting throughout 2025, but many didn’t because the forms weren’t finalized until late in the year.
The car loan interest deduction creates its own complications. Taxpayers need loan statements showing interest paid in 2025, and many lenders haven’t updated their reporting to distinguish between qualifying and non-qualifying interest.
Parents can now establish Trump Accounts—a new type of individual retirement account for children. The IRS created a dedicated website, trumpaccounts.gov, to handle enrollment.
The contribution limits and distribution rules differ from traditional IRAs, and the tax advantages accumulate over decades. Families with children should evaluate whether these accounts fit their wealth transfer and education funding strategies.
The executive order “Modernizing Payments To and From America’s Bank Account” sounds bureaucratic until you realize what it means: the IRS is killing paper refund checks. Taxpayers without bank accounts face a choice between opening one or waiting months for alternative payment methods.
Small businesses that historically received paper checks for overpayments need to establish direct deposit immediately. The IRS won’t hold your refund indefinitely while you figure out banking logistics.
Form 1099-K now reports payment card and third-party network transactions with lower thresholds than previous years. Businesses using Venmo, PayPal, or similar platforms for commercial transactions will receive these forms, triggering reporting requirements many aren’t prepared for.
Form 1099-DA is entirely new—it reports digital asset proceeds from broker transactions. Anyone who traded cryptocurrency, NFTs, or other digital assets through a broker in 2025 will receive this form and must report the transactions on their return.
The problem: many taxpayers don’t understand which transactions trigger reporting, leading to underreported income and subsequent IRS inquiries.
The standard six-month extension for individual and C corporation returns moves the deadline to October 15. Partnerships and S corporations get extensions to September 15. Trusts extend to September 30.
But extensions don’t extend payment deadlines—estimated tax must be paid by the original deadline, or penalties accrue. Businesses facing complex OBBBA reporting should consider filing extensions to avoid rushed returns with errors due to the changes in tax law.
Estimated tax payments for Q1 2026 C Corporations are due April 15, the same day as 2025 returns. CFOs managing cash flow need to balance current-year obligations with prior-year settlements.
For C Corporations, Q2 2026 estimated payments are due June 15. Q3 payments hit September 15. These deadlines haven’t changed, but the OBBBA provisions affecting 2026 income require businesses to recalculate estimated tax obligations based on new deductions and credits.
The problem: many businesses won’t finalize their 2025 returns until summer, making accurate 2026 estimates very difficult without proactive modeling.
Form 5500 for employee benefit plans is due July 31, 2026. The OBBBA’s changes to dependent care benefits and retirement account rules require updated plan documentation and reporting.
Businesses that increased dependent care FSA limits to the new $7,500 maximum need Form 5500 filings reflecting those changes. Plans that didn’t update in 2025 face compliance issues this summer.
First, audit your 2025 payroll records. Do you have clear documentation separating tip income, overtime compensation, and regular wages? If not, reconstructing that information in April is exponentially harder than organizing it now.
Second, communicate direct deposit requirements to employees expecting refunds. The IRS won’t accommodate paper check requests—employees without bank accounts need solutions before filing.
Third, model your estimated tax obligations for 2026, incorporating OBBBA provisions. Waiting until April to calculate Q1 payments could expose them to underpayment penalties.
Fourth, review your employee benefit plan documentation. The July Form 5500 deadline arrives faster than you expect, and correcting plan documents retroactively is expensive.
The 2026 filing season introduces more complexity than any year since the Tax Cuts and Jobs Act implementation. The difference: in 2018, businesses had months to prepare. In 2026, the OBBBA passed mid-year, leaving limited time for systems updates and process changes.
The IRS claims it’s ready. The real question is whether your business is ready. The filing deadline hasn’t changed, but everything about how you prepare for it has.
Need help navigating the 2026 filing season and OBBBA compliance? Wiss’s tax team has already processed hundreds of returns under the new rules. We know where the problems are hiding and how to avoid them. Let’s make sure your filing season is boring—in the best possible way.