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We Do Books™ Blog

Michael DiSabatino of We Do Books™ shares expert insights to help you unlock your business's full potential by delivering proven strategies for maximizing tax savings, streamlining operations, and driving sustainable growth.

The information provided on this site is for general informational purposes only and should not be construed as professional financial, tax, or legal advice. For advice tailored to your specific situation, we recommend consulting with a qualified professional. We Do Books is here to assist by calling 855-922-WeDo (9336)

The IRS Fresh Start Program: Separating Fact from Gimmickry

IRS Fresh Start: The Reality Check

Don't let tax debt keep you in the dark. The IRS Fresh Start initiative offers genuine avenues for relief, but it’s not a magic trick. It requires careful navigation and compliance. Think of it as a well-lit path toward financial stability—if you have the right map.

While marketing emails might make it sound like an automatic "get out of debt free" card, the reality is that the program streamlines existing IRS tools, such as Offers in Compromise, Installment Agreements, and tax lien relief. To find your way through, you must meet specific criteria, provide detailed financial information, and stay current on future filings.

Success isn't about wishing your debt away; it’s about strategic action and professional guidance. Taking a reality check on your situation is the first step toward a clearer, secure financial horizon. Let WeDoBooks.com help you find the way.

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When One Dollar of Income Can Cost You $18,000: The ACA Subsidy Cliff Returns in 2026

ACA Subsidy Cliff 2026: How Exceeding 400% of Poverty Can Trigger Premium Tax Credit Repayment

Why a Small Income Miscalculation Could Trigger a Big Tax Bill

For several years, the Affordable Care Act (ACA) marketplace included a safety feature that helped taxpayers avoid catastrophic repayment of health insurance subsidies.

That protection is scheduled to expire after 2025, meaning the original ACA rules return beginning in 2026.

For taxpayers who carefully manage their income to qualify for premium subsidies, this change matters more than most people realize.

And unfortunately, we see the consequences every year in tax season.

Clients often receive advance premium credits based on income estimates provided during enrollment. If those estimates turn out to be wrong, the IRS reconciliation process can produce an unexpected tax bill.

Starting in 2026, the risk becomes significantly larger.

The Subsidy Cliff Is Back

Under the temporary pandemic rules, taxpayers could qualify for ACA premium subsidies even if their income exceeded 400% of the Federal Poverty Level (FPL).

That temporary rule disappears after 2025.

Beginning in 2026, the original ACA rule returns:

  • If your Modified Adjusted Gross Income (MAGI) exceeds 400% of the federal poverty level, you lose eligibility for the premium tax credit entirely.

Not just part of it.
All of it.

That means if your income crosses the threshold by even one dollar, the IRS can require repayment of the entire subsidy received during the year.

Repayment Caps May No Longer Protect You

Another pandemic-era protection limited how much taxpayers had to repay if their income estimate turned out to be wrong.

Those caps softened the impact of miscalculations.

Beginning in 2026, those protections disappear.

Taxpayers who underestimated income may be required to repay the entire excess premium credit received during the year.

There is no built-in limit.

A Realistic Example

Consider a married couple receiving $1,500 per month in ACA subsidies.

That equals:

  • $18,000 per year in advance premium credits.

If their income estimate during enrollment projected them under 400% of the poverty level, they would qualify for those credits.

But suppose their actual income increases late in the year due to:

  • A profitable business quarter
  • A Roth conversion
  • Investment gains
  • Sale of assets

If their final MAGI crosses the 400% threshold, the IRS reconciliation could require repayment of the entire $18,000 subsidy.

All of it.

Who Is Most At Risk

This rule change will disproportionately affect taxpayers whose income fluctuates during the year. The groups most commonly affected include:

  • Early retirees
    People living on savings often manage withdrawals to stay within ACA subsidy ranges.
  • Self-employed business owners
    A strong fourth quarter or unexpected contract can push income over the limit.
  • Investors managing tax strategies
    Capital gains harvesting or Roth conversions can unintentionally trigger the subsidy cliff.
  • Taxpayers relying on enrollment estimates
    Many people rely on income projections created during insurance enrollment rather than working with tax professionals.

The Problem We See Every Tax Season

In practice, we frequently see ACA repayment issues caused by inaccurate income estimates during marketplace enrollment.

Those estimates are often produced by insurance brokers or sales representatives who do not have full visibility into a client's tax situation.

When the tax return is eventually prepared, the reconciliation occurs on Form 8962, and the difference becomes immediately visible.

In some cases, taxpayers must repay thousands of dollars.

Beginning in 2026, the potential repayment exposure becomes significantly larger.

Planning Matters More Than Ever

With the subsidy cliff returning, managing Modified Adjusted Gross Income (MAGI) becomes essential for taxpayers using ACA marketplace coverage.

That includes planning around:

  • Roth conversions
  • Capital gains
  • Business income timing
  • Retirement withdrawals
  • Bonus or contract income

In many cases, the difference between careful planning and a surprise income spike could determine whether a taxpayer keeps or repays their ACA subsidy.

Final Thought

Health insurance subsidies can be extremely valuable, but they come with complex tax rules.

When income estimates are wrong, the IRS reconciliation process can turn those subsidies into a tax liability.

With the return of the ACA subsidy cliff in 2026, proactive tax planning becomes even more important for taxpayers whose income varies during the year.


This publication provides summary information regarding the subject matter at time of publishing. Please call with any questions on how this information may impact your situation. This material may not be published, rewritten or redistributed without permission, except as noted here. All rights reserved.

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10 Sources of Tax-Free Income

What Everyone Should Know

Wouldn't it be nice to have a source of nontaxable income?

You may be more fortunate than you realize.

Listed here are a number of income items that the IRS does not tax.

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Tax Surprises for the Newly Retired

You've got it all planned out. Your retirement savings accounts are full, you have started receiving Social Security benefits and your pension is ready to go. Everything is planned. What could go wrong?

Here are five surprises that can turn your plan on a dime.

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OBBBA: "No Tax on Tips" — What Actually Changes

OBBBA adds a temporary, targeted deduction for tips. It is not a universal no tax on tips. Many tipped amounts are still taxable, and payroll taxes still apply.

Here is the clean, CFO-level breakdown:

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Net Unrealized Appreciation (NUA): A Little-Known Tax Strategy for Company Stock in Retirement Plans

Net Unrealized Appreciation (NUA): A Tax Opportunity Hidden Inside Some Retirement Plans

Many employees accumulate company stock inside their retirement plans over the course of their careers. When retirement approaches, that stock may qualify for a little-known tax treatment called Net Unrealized Appreciation (NUA).

When handled correctly, NUA can significantly reduce the tax burden associated with distributing company stock from a retirement plan. When handled incorrectly, the opportunity disappears and the entire distribution may become taxable as ordinary income.

Understanding the mechanics of NUA is therefore important before taking any action with employer stock held inside a retirement account.

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Do You Need to File a Tax Return?

Getting This Wrong Can Cost You

One of the more common tax questions is whether you need to file a federal tax return this year. The answer is: it depends. But not filing a tax return when you should can cost you plenty, especially with the passage of a major piece of tax legislation like the One Big Beautiful Bill Act. Here are some quick tips to help you determine your answer.

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NON-Retiree Retirement Ideas

Want money when you retire?

Here are some tips.

Here are five common retirement planning tips and what you can do to take advantage of them. The key is retirement planning starts today, not decades from now when you are reaching retirement age.

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Your Home — A Bundle of Tax Benefits

There are many tax benefits built into home ownership. Here's a summary of the most common.

It may be worth a quick review to ensure you are maximizing your home ownership tax benefits.

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NEW FREE MONEY! — Trump Accounts for Kids

The New Child Savings Plan Parents Need to Know (530A / “Invest America”)

Congress has officially blessed us with yet another account type. This one is built for children and is commonly being called a “Trump Account” (also referred to as a Section 530A / “Invest America” account). The elevator pitch: it’s a tax-advantaged, long-term investment account for a minor, seeded (in some cases) with government money, and designed to push families toward early investing.

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2026 Gambling Taxes — The IRS Just Added a 10% "House Edge" to Your Losses

If you’ve gotten used to reporting gambling winnings and then “washing them out” with gambling losses on your tax return, 2026 is where that muscle memory can betray you. A federal law change effective for tax years beginning after December 31, 2025 rewrote the wagering-loss rule in IRC §165(d) so the deductible amount is now generally 90% of your wagering losses, and it’s still capped at your wagering gains (winnings). Translation: even a break-even gambling year can create taxable “phantom income” that you’re not accustomed to seeing.

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The Hobby Loss Rule — Rodeo Edition (Internal Revenue Code §183)

The IRS doesn’t care how exciting your rodeo belt buckle is… they care whether you’re engaged in the activity with the actual intent to make a profit.

If it’s a business, losses are deductible.

If it’s a hobby, deductions are limited and can’t create a net loss against other income.

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Five Big Tax Mistakes — Don't Let Them Happen to You!

Every year taxpayers are hit with tax surprises that could be avoided if they just knew the rules.

Here are five big ones that are easy to avoid with some simple planning.

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GREAT! You Have a Large Refund — Now What?

For some reason, some believe it's better to receive than to give when it comes to filing taxes.

While that may help your savings account, it's not always a great idea. Here's why:

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Tax-Free Rental of Your Property

Most income you receive is taxable income that is reported to the federal and state tax authorities. However, renting out your home or vacation property on a short-term basis can be done tax-free if you follow the rules.

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Gone Phishing?

Each year the IRS publishes the top dozen tax scams it encounters over the prior year. One of them that makes an all too common appearance on their list is the phishing scam.

Here is what you need to know.

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Common Overlooked Taxable Events

Some issues fly under the radar until they trigger an unexpected tax return notice, penalty, or tax bill. What may seem like routine financial activity can quickly turn into a costly mistake if it’s reported incorrectly.

Below are seven commonly misunderstood tax situations that deserve careful attention before filing.

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Understanding Tax Terms — Head of Household

The tax term head of household is one of the more misunderstood tax phrases inside the U.S. tax code.

However, if your situation warrants head of household status, there are two big tax benefits:


First, a higher standard deduction.

Second, lower effective tax rates for virtually every income level.

This is great, but only if you qualify.

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Personal Exemptions Gone Plus $6,000 New Deduction

What Everyone Should Know

The recently passed One Big Beautiful Bill Act (OBBBA) addresses some tax law uncertainty while creating several benefits impacting your 2025 tax return. One of these benefits is a new $6,000 deduction for seniors. Here is what you need to know.

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The IRS Says Late Filing of S Corporation and Partnership Returns Can Be Costly

The IRS is penalizing late filers of S corporation and partnership tax returns. This despite the fact that late filing of the tax returns (Forms 1120S and 1065), due March 15th, often does not impact the receipt of the taxes due on April 15th. Those that are getting this penalty are often couples and other small firms who have formed these business entities to provide legal protection for their shareholders.

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