Frequently Asked Questions

On the Virtue of Extensions

Trust me when I say this: I understand the hesitation when it comes to the idea of filing an extension for your tax return. Even though I’ve been preparing returns professionally for 14 years, I absolutely dread filing my own tax return. As a tax expert and Enrolled Agent with the IRS, even I can’t escape the grueling anxiety and uncertainty leading to the moment when I finally submit my return for the year. Am I forgetting donations? Did I include all of my business mileage? Why can’t I claim Peanut, my tiny toy poodle, as a dependent? To relieve these anxieties, rushing to e-File my tax return is the metaphorical equivalent of shoving everything into the closet and calling my room clean. 

For these reasons, I almost always file an extension. Whether I’m expecting a refund or know that I owe, the pressure of rushing to complete my return puts me at risk of filing an inaccurate return that will later require an amendment. For most people, hurrying through a tax return produces more anxiety than taking a standardized test. Taxes involve highly personal information, large sums of money, and the risk of going to prison. In this frazzled mindset, it’s easy to make mistakes, give up, guesstimate, or miss opportunities that could save you money.

According to the utilitarian philosopher Jeremy Bentham, the outcome that produces the greatest good for the most people can be mathematically measurable. Whether the United States tax system operates under a social contract, categorical imperative, utilitarianism, or moral realism, it is not ultimately relevant to a discussion of filing an extension. Regardless of the ethical framework, the virtues of accuracy empirically outweigh the virtues of timeliness when a government, endeavoring to be fair, depends primarily upon tax revenues to balance its budget.

Bentham once wrote on the subject of felicific calculus:

Intense, long, certain, speedy, fruitful, pure—

Such marks in pleasures and in pains endure.
Such pleasures seek if private be thy end:
If it be public, wide let them extend
Such pains avoid, whichever be thy view:

If pains must come, let them extend to few.

The utilitarian pros and cons of filing and paying taxes by a specific date is not an ethical argument about rights and responsibilities; an automatic extension period is provided by the Internal Revenue Service with clear legal parameters. While paying taxes is a responsibility, doing so under a veil of deadline-driven ignorance trivializes the complexities of the tax code. Taxes are difficult. By encouraging over 150 million taxpayers to participate at the same time, a carnival of errors ensues: there is no parking, the entrance becomes dangerously overcrowded, the Ferris Wheel breaks under pressure, the restrooms turn into Lord of the Flies, and instead of enjoying funnel cakes, we end up with an overpriced hot mess on our hands.

In any overloaded system attempting to maximize attendance, quality control suffers, critical systems falter, and arguments in favor of fair and accurate taxation are frequently reduced to a matter of adherence to the law for the sake of avoiding punishment. By this, I mean that the sheer volume of filings that are rushed to completion create inequalities in the system, and trigger a cascading imbalance that penalizes the majority of taxpayers for their obedience. While tax fraud has steadily increased, enforcement has fallen further behind, handled increasingly by computerized systems searching for inaccurate digits and missing documents rather than deliberate tax evasion.

Whether or not you prize accuracy over timeliness, let me compare the pros of rushing to file your tax return with the pros of filing for an extension.

Rushing to File a Timely Return:

◦ Pro: it’s over! You get money back, or at least feel like you know what you owe. Adulting feels great, and closure is psychologically rewarding.

◦ Pro: if there’s a problem, the sooner you know, the better! If you’re underwithholding at work, you have more time to correct course and prevent recurring issues.

◦ Pro: Avoiding penalties and interest. If you file on time, you are less likely to incur a failure-to-file and/or failure-to-pay penalty. If you owe money, you still need to pay with your extension. If you haven’t done the proper work to calculate your projected tax liability, filing an extension alone will not remove the failure-to-pay penalty. Due to this, you might have to do most (or all) of the work to determine how much to pay with your extension. If doing this projection work isn’t possible, you might need to overestimate in order to completely cover the liability.

Filing an Extension:

◦ Pro: Rushing leads to errors. JFK once said “an error doesn’t become a mistake until you refuse to correct it.” If you perpetually find yourself filing at the last minute, your errors will become mistakes, and these mistakes can be costly. Would you rather overpay because you were in a hurry, or pay the right amount? How about underpay because you were in a hurry, but get a letter from the IRS, or worse, get audited?

◦ Pro: You are more likely to find a willing professional at a fair price. Rushing your CPA or accountant during their busiest season is a lesson in supply-side economics, and returns filed closer to the deadline will typically cost more than filing with a professional when demand is reduced.

◦ Pro: When handled correctly, extensions remove the majority (or all) penalties and interest incurred from failing to file and/or pay by the deadline. An extension puts the game into overtime, and lets you focus on developing a winning strategy with additional time, energy, and focus.

◦ Pro: Fewer amendments, letters, and audits. Many people believe that filing an extension will “flag their return,” and worry that extensions could get them in trouble. I assure you that the reason for allowing automatic timely extensions is that the IRS is looking to collect the right amount of tax from you; not a dollar more or a dollar less.

◦ Pro: It’s easy, free, and automatically accepted! Unlike filing your actual tax return, filing an extension takes very little time and effort; for most filers, all you need is your name, birthday, social security number, and address. There are free IRS worksheets, professional firms, online software providers, and estimated tax calculators to help you estimate how much to pay with your extension to avoid any interest and/or penalties you might incur. If this doesn’t work, the IRS says pay a “reasonable” estimate of what you think you might owe. How you arrive at this reasonable estimate is ultimately up to you, but be prepared to defend it if you underestimate. Any amount you overpay would be refunded to you when you file your return, so it might be better to err on the side of caution if the failure-to-pay penalty would be significant.

The list goes on, but I believe you understand my position: extensions are your friend. They give you access to more time and resources to ensure you’ve gotten everything right. This extended timeframe might be as long as six months, or even longer in special circumstances like illness/confinement, natural disasters, or deployment in a combat zone. Since some tax documents might get lost in the mail, or are received/corrected after you’ve already filed, you have more time to ensure that you are filing with the highest degree of accuracy, and therefore, the lowest degree of risk.

If you want to file an extension, many professionals offer this as a free service. They will work with you on setting an appropriate deadline, and help you finish your return as quickly and accurately as possible regardless of the extended deadline. If 50 million Elvis fans can’t be wrong, then 150 million taxpayers can’t be right. Sometimes fools wait and wise people rush in. Either way, if you aren’t 100% sure you will have everything ready by April 15th, 2026, don’t be afraid to call a time-out on taxes.

Here are some of the ways you can file an extension: go on the IRS.gov webpage, utilize the IRS2Go App, use an online software provider like TurboTax, H&R Block, TaxAct, or Taxslayer, or send your request in by mail using Form 4868. We set up this link to file an extension with TaxAct, a free process that takes only a few minutes (comes with some nifty discounts and perks as well if you do want to file your taxes with them): www.taxact.com/partner/wolverine

Remember that you may owe taxes and want to make a payment with your Extension to avoid the risk of interest and/or penalties. This calculator set up by the IRS will help you compute an estimated balance due to help you make a timely payment with your extension. It takes into account the changes from the OBBBA that went into effect in 2025, making it a very helpful tool. As a general rule of thumb, it might be wise to multiply the amount by 1.1 just to be on the safe side. Calculator: https://www.irs.gov/individuals/tax-withholding-estimator

If you want help from Wolverine Tax with an extension, call or text us today at 734-999-1040, or e-mail us at info@wolverinetax.com with the word “EXTENSION” and we’ve got you covered.

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