Tax Breaks: The Surprise Refunds And Lingering Tax Bills Edition
Tax season is (mostly) over, but we’re still talking about refunds. But this time, the chatter isn’t about refunds tied to the 2025 tax year, but for those well before then.
A recent federal court decision in Kwong v. United States could open the door for taxpayers to claim refunds of penalties and interest tied to the COVID-19 period. The court held that under Section 7508A, tax deadlines were automatically paused for the entire duration of the federally declared disaster (January 20, 2020–May 11, 2023), plus an additional 60 days. That interpretation extends the statute of limitations for certain refund and abatement claims—potentially giving taxpayers until July 10, 2026, to act.
This creates an opportunity for individuals and businesses who were assessed failure-to-file or failure-to-pay penalties (or related interest) during that window to seek relief. However, the decision is not final and may be appealed, meaning taxpayers may want to file “protective claims” now to preserve their rights. Even then, success isn’t guaranteed—Kwong itself resulted in only a partial recovery—so careful evaluation of each claim is essential.
A less fun conversation for many taxpayers is figuring out how to actually pay what they owe—and the IRS offers more flexibility than people might expect. Taxpayers who can pay in full have lots of options, including check or money order, direct bank payments through IRS Direct Pay, debit or credit cards (with fees), digital wallets, cash at participating retailers, or even wire transfers. Each method has its own limits and considerations, but the key takeaway is that paying electronically is increasingly the norm, even as traditional options like checks remain available for now (fun fact: the IRS won’t accept single checks or money orders for $100 million or more).
For those who can’t pay right away, there are still options. The IRS offers installment agreements to pay over time, offers in compromise for qualifying taxpayers who truly can’t pay in full, and temporary collection delays in certain circumstances. Interest and penalties may continue to accrue, but taking action—rather than ignoring the bill—can prevent more serious consequences.
The IRS now also provides a Tax Debt Help tool that walks taxpayers through their options, making it easier to choose the best course based on their financial situation. I gave it a whirl, and it’s surprisingly useful.
For some taxpayers, the key to avoiding owing taxes is to use tax-planning strategies, like tax-harvesting. Investors have long used tax-loss harvesting to offset gains, but a growing body of research suggests that exchange-traded funds (ETFs) may be creating a workaround to the IRS wash sale rules. While the law disallows claiming a loss if you repurchase the same or “substantially identical” security within 30 days, the definition of “substantially identical” is murky—especially for ETFs that track nearly identical indexes. A recent study found that institutional investors are increasingly swapping highly correlated ETFs to realize losses without meaningfully changing their market exposure, generating an estimated $84 billion in losses over time. The findings highlight a gap between the intent of the wash sale rule and modern investment practices, raising questions for both taxpayers and policymakers.
You can also lower your tax bill by taking advantage of tax breaks at the office—like employer-funded health care and retirement plans. But while many workers can take advantage of a retirement account, the Mega Backdoor Roth is a strategy designed for high earners who have already maxed out their standard 401(k) contributions. It works by allowing after-tax contributions to a 401(k) (beyond the usual deferral limits) and then converting those funds into a Roth account. If structured correctly, this can allow up to $47,500 per year to be shifted into a........
