The 2026 tax filing season is giving financial advisors an early look at how taxpayers are navigating the first year of major changes under the One Big Beautiful Bill Act (OBBBA).
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New data from online expert platform JustAnswer, which analyzed nearly 23,000 tax-related questions submitted so far this year, shows that Americans are turning to experts in growing numbers as they prepare their returns. The overall volume of tax questions is trending nearly 10% higher than the same period in 2025, suggesting an unusually uncertain early filing season.
The questions highlight where clients are struggling most as they file under new rules for the first time. Three areas stand out in particular: reporting income from multiple sources, understanding new deductions introduced by the OBBBA and navigating retirement-related tax rules.
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Income reporting confusion surges
The biggest jump in taxpayer questions this filing season centers on income reporting.
According to JustAnswer’s analysis, questions tied to income sources such as freelance work, gig earnings and digital payments are up 118% year over year. That increase makes income reporting the fastest-growing tax topic so far this season.
The surge reflects broader changes in how Americans earn income. Nearly 40% of Americans today have a side hustle or rely on supplemental income from freelance earnings, according to a survey from LendingTree, an online loan marketplace company.
Patrick Huey, an accredited tax preparer and the founder of Victory Independent Planning in Camas, Washington, said many of his longtime W‑2 clients and some retirees now have at least one side hustle — typically photography, short‑term rentals or consulting — and that’s where most of their questions are coming from.
“They’re used to a world where the employer handles all the tax plumbing. Suddenly, they’re getting 1099s, platform statements or app‑based payments, and they’re not sure what’s business income, what’s a hobby or what’s ‘just Venmo,'” Huey said. “Under OBBBA, gig‑economy and digital‑payment income is more squarely on the IRS’s radar. Lower reporting thresholds and clearer guidance mean more of this activity will be reported, whether people are ready or not.”
Shifting IRS policies around digital payment reporting have added to the uncertainty. In recent years, the agency has changed or delayed rules governing when platforms must report payments to taxpayers and the IRS, leaving many filers unsure about what forms they should expect or what income must ultimately be reported.
For financial advisors, the trend underscores how the growth of gig work and freelance income is complicating tax planning for many clients. Even relatively modest side income can create reporting requirements that taxpayers may not fully understand without professional guidance.
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New OBBBA deductions driving questions
The second major area of confusion involves deductions tied to new provisions of the OBBBA.
JustAnswer found that questions about the standard deduction increased 154% compared with the same period last year, while questions referencing new tax laws or rule changes rose 155%, the largest relative increase of any category tracked by the platform.
The legislation introduced tax breaks tied to tips, overtime pay and car loan interest, many of which can be claimed even by taxpayers who do not itemize deductions.
Advisors say the rollout of these provisions has not been entirely smooth.
Lawrence Pon, a CPA and financial planner at Pon & Associates in Redwood City, California, said there’s a lot of confusion with clients concerning new deductions for tips and overtime pay.
“Qualified overtime is defined by the Federal Labor Standards Act (FLSA), Section 7. Many workers get overtime that is not FLSA qualified, such as union workers or state overtime. For example, in California, you get overtime when you work more than eight hours in a day. That does not count for the overtime deduction because it was not paid in excess of a 40-hour work week. This is causing great confusion.”
“Employers are not providing this information or, if they do, it may be incorrect,” he added. “Us tax professionals need to study the year-end pay stub carefully and quiz our clients about their overtime.”
Last week, the IRS also issued revised instructions for the tips deduction. Pon said such a mid-season change could create problems for early filers whose returns may now need corrections.
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Retirement questions remain top of mind
While new rules are driving the biggest spikes in taxpayer confusion, retirement-related tax questions remain a consistent area of interest.
JustAnswer’s data shows that topics such as IRA contributions, 401(k) limits, Roth versus traditional contribution strategies and qualified charitable distributions (QCDs) continue to rank among the most frequently discussed tax topics on the platform.
Alongside those evergreen considerations, advisors say they’re also handling significant misconceptions among clients regarding the new senior deduction, which allows individuals aged 65 and older to claim an additional $6,000 deduction ($12,000 for married couples if both qualify).
“Under OBBBA, what changed is not that benefits suddenly escape taxation; it’s that seniors get a more generous standard deduction and an additional ‘senior’ deduction that can soften the blow,” Huey said. “Up to 85% of Social Security can still be taxable depending on total income. Clients hear ‘lower taxes for seniors’ and sometimes mentally translate that into 2024’s campaign promise of ‘my Social Security won’t be taxed anymore,’ which just isn’t true.”
Pon said that confusion — often perpetuated by politicians claiming there’s no tax on Social Security — can have costly consequences for clients, who in some circumstances make themselves ineligible for the new senior deduction through poorly timed Roth conversions.
Those complexities are making efficient tax planning a multi-year endeavor, Huey said.
“Even for ‘plain vanilla’ households, the combination of more 1099 income, OBBBA’s more layered deduction landscape … and longer retirements has pushed us out of the era of one‑year tax thinking,” Huey said. “The best advice isn’t a single trick; it’s an approach: Assume your tax life now has multiple moving parts, and build a three‑ to five‑year plan for where to save, when to recognize income and how to coordinate things like the senior deduction, QCDs and Roth conversions, instead of hoping it all lines up by accident when the W‑2s and 1099s arrive.”
