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IRS Wraps Up 2026 Tax Forums — Here’s What Tax Pros Were Told About the 2027 Filing Season

October 5, 2026 by Amanda Blankenship Leave a Comment

2027 tax filing season
Nearly 13,000 tax professionals attended the IRS’s five 2026 Nationwide Tax Forums, where sessions covered the 2027 filing season, tips and overtime provisions, digital assets, audits and collection cases. grandbrothers/Shutterstock

Nearly 13,000 tax professionals attended IRS events across five U.S. cities this year, getting an early look at issues that could affect taxpayers when the 2027 filing season arrives.

The Internal Revenue Service announced Sept. 21 that it had completed its 2026 Nationwide Tax Forum series after holding its fifth and final event in San Diego.

The five forums brought together enrolled agents, certified public accountants, attorneys and other tax professionals for workshops, seminars and opportunities to speak directly with IRS personnel.

Although the events are designed primarily for tax professionals, many of the issues discussed—including new tax provisions, digital-asset reporting, IRS audits and collection cases—can eventually affect the taxpayers whose returns those professionals prepare.

For taxpayers already thinking about next year’s return, the subjects receiving attention at the forums provide a useful preview of issues tax preparers are preparing to handle during the 2027 tax filing season.

Nearly 13,000 Tax Professionals Attended Five Events

The IRS held its 2026 Nationwide Tax Forums in Chicago, New Orleans, New York, Orlando and San Diego between July and September.

Each three-day IRS Tax Forum offered seminars and workshops covering federal and state tax issues, IRS procedures and emerging developments affecting tax preparation.

More than 40 seminars and workshops were offered, and qualifying attendees could earn continuing education credits while participating.

IRS Chief Executive Officer Frank J. Bisignano said the events allow the agency to receive feedback from tax professionals while providing information about emerging tax policies.

That two-way communication matters because tax preparers often see practical problems with new tax laws and IRS procedures while working directly with millions of individual taxpayers.

More Than 1,100 Tax Cases Were Resolved

The forums weren’t limited to classroom-style presentations.

Each event included a Case Resolution Room operated by the IRS and the Taxpayer Advocate Service, where qualifying tax professionals could bring particularly difficult client cases for one-on-one assistance.

According to the IRS, 1,165 taxpayer cases were resolved across the five events.

The Taxpayer Advocate Service explains that specialists research cases brought to the program and work to resolve the tax matter, with TAS able to open a case for additional work when an issue can’t be completed during the appointment.

For taxpayers dealing with complicated IRS problems, those numbers illustrate one of the practical roles tax professionals can play beyond simply preparing and electronically filing an annual return.

Digital IRS Accounts Were Another Major Focus

Tax professionals also received help navigating the IRS’s increasingly digital services.

The agency says 1,635 tax professionals received assistance through Digital Account Services Rooms during the five forums.

Help included IRS e-services, Preparer Tax Identification Numbers, commonly known as PTINs, and identity authentication.

These systems can matter to consumers because legitimate paid federal tax return preparers generally must have a valid PTIN, and tax professionals increasingly use IRS digital tools when representing or assisting clients.

Taxpayers choosing someone to prepare a 2026 return can use the IRS’s online resources to understand preparer credentials and should be wary of anyone unwilling to sign a return or provide a valid PTIN when one is required.

Tips and Overtime Were Among the Topics Discussed

The forums also devoted multiple sessions to tax changes under the Working Families Tax Cuts.

According to the IRS, sessions covered provisions commonly described as “no tax on tips” and “no tax on overtime,” along with information about what tax professionals should expect during the upcoming 2027 filing season.

Those provisions can be particularly important for workers whose income includes qualifying tips or overtime because understanding eligibility and maintaining appropriate records can affect what ultimately appears on a federal tax return.

The forums gave tax professionals an opportunity to learn how the IRS is approaching implementation before millions of taxpayers begin filing 2026 returns.

Anyone who thinks a new tax provision may apply to their household should verify the requirements rather than assuming every dollar labeled as a tip or overtime payment automatically receives identical federal tax treatment.

Cryptocurrency and Digital Assets Remain on the IRS Radar

Digital assets were another subject receiving attention during the 2026 forums.

Seminars addressed digital-asset information reporting, an increasingly relevant issue as taxpayers buy, sell, exchange or receive cryptocurrency and other digital assets.

That matters financially because failing to understand the tax treatment of a transaction can lead to an incorrect return, an unexpected tax bill or the need to amend a return later.

Taxpayers who have digital-asset activity should keep transaction records rather than waiting until tax season and expecting a preparer to reconstruct an entire year of purchases, sales and transfers.

The fact that digital-asset reporting appeared among the IRS’s highlighted forum topics is another reason taxpayers with cryptocurrency activity should expect it to remain an important compliance issue during the 2027 tax filing season.

IRS Audits and Collection Cases Were Also Covered

Tax professionals also attended sessions on navigating IRS audits and managing collection cases.

Those subjects can become expensive for taxpayers when unresolved tax balances accumulate interest and penalties or when a complicated audit requires substantial professional assistance.

Good recordkeeping can therefore have a direct financial payoff, particularly for taxpayers claiming deductions or credits that may require supporting documentation.

Rather than scrambling for receipts, statements and tax forms months or years later, taxpayers can create a digital or paper tax file now and add important documents throughout the year.

A little organization before filing season can make preparing a return easier and potentially reduce professional fees if your accountant doesn’t have to spend additional time tracking down missing information.

Start Preparing for the 2027 Filing Season Now

The IRS forums may have ended, but the issues discussed at them are moving directly toward taxpayers as the next filing season approaches.

Changes involving tips and overtime, digital-asset reporting and other tax provisions mean some households may encounter questions on their 2026 returns that they didn’t face previously.

If you use a tax professional, waiting until filing season is underway to ask about a complicated new tax situation can leave less time to gather documents or correct recordkeeping problems.

The IRS Nationwide Tax Forum program is primarily professional education, but the nearly 13,000 attendees represent accountants, enrolled agents and other practitioners preparing for the real-world tax questions their clients will soon bring them.

For taxpayers, the financial takeaway is straightforward: organize records now, understand which tax changes could affect your household and don’t wait until you’re ready to hit “file” to discover that you’re missing information needed for your 2026 return.

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Headshot of Amanda Blankenship
Amanda Blankenship

Amanda Blankenship is the Chief Editor for District Media.  With a BA in journalism from Wingate University, she frequently writes for a handful of websites and loves to share her own personal finance story with others. When she isn’t typing away at her desk, she enjoys spending time with her daughter, son, husband, and dog. During her free time, you’re likely to find her with her nose in a book, hiking, or playing RPG video games.

Filed Under: news Tagged With: 2027 tax filing season, cryptocurrency, digital assets, IRS, IRS audits, overtime, Tax Deductions, tax preparation, Tax Professionals, tax returns, taxes, tip income

Made Money From a Side Hustle in 2026? Don’t Confuse a 1099-K With What You Actually Owe the IRS

October 1, 2026 by Brandon Marcus Leave a Comment

Made Money From a Side Hustle in 2026? Don’t Confuse a 1099-K With What You Actually Owe the IRS
A 1099-K reports gross payment transactions, not necessarily taxable profit. Side hustlers should reconcile the form with refunds, eligible business expenses, and records of personal-item sales before filing their tax returns – Shutterstock

A 1099-K can make a profitable side hustle look more lucrative than it really was. If payment apps, online marketplaces, or gig platforms report thousands of dollars in transactions, that figure does not automatically represent taxable profit or the amount owed to the IRS.

This matters for anyone selling handmade goods, flipping furniture, freelancing, or accepting payments through digital platforms. A payment report tracks transactions, while your tax return must account for what you earned, which expenses qualify, and what the transactions actually involved. Confuse those figures, and you could overstate your income, overlook a tax obligation, or miss deductions you legitimately qualify for.

The Number on Your 1099-K Tells Only Part of the Story

Form 1099-K reports certain payments processed through third-party settlement organizations and payment cards. Platforms may send the form to the IRS and the recipient when applicable reporting requirements apply. The reported amount generally reflects gross payments, not the profit left after expenses.

Consider a hypothetical online seller who receives $8,000 through a marketplace during the year. That figure might include $5,000 from handmade products, $1,500 from selling personal belongings, and $1,500 in refunded transactions or other adjustments. The seller cannot simply treat the entire amount as business profit without examining the underlying transactions.

The platform’s reporting figure may also exclude or handle certain adjustments differently from the seller’s own records. Fees, shipping costs, refunds, and the original cost of merchandise can all affect the financial picture. A 1099-K supplies useful information, but it does not prepare the seller’s tax return.

The first job is matching reported payments to actual transactions. That reconciliation helps separate business receipts from personal sales, refunds, transfers, and other amounts that require different treatment.

Business Expenses Can Change the Taxable Amount

A side hustle’s revenue rarely tells the whole financial story. Someone who earns money repairing bicycles, for example, might buy replacement parts, pay marketplace fees, purchase business supplies, and cover shipping costs. Eligible ordinary and necessary business expenses can reduce the profit that the business reports to the IRS.

For a sole proprietor, Schedule C generally captures business income and deductible expenses. The resulting net profit, rather than the raw payment total, helps determine the business’s contribution to taxable income. Personal expenses do not qualify simply because the side hustle needs money.

Good records make this calculation much easier. Keep receipts, invoices, transaction histories, and statements showing platform fees and refunds. If a purchase serves both business and personal purposes, determine the business portion instead of automatically deducting the entire cost.

Consider a hypothetical freelancer who receives $6,000 through a payment platform and spends $900 on qualifying business expenses. Before considering other adjustments, the freelancer’s business profit would be $5,100. That does not mean the freelancer owes $5,100 in taxes. It means the calculation starts with a more accurate measure of the money earned.

Selling Old Belongings Is Different From Running a Business

A closet cleanout can produce a surprising payment-app total, especially when someone sells furniture, electronics, collectibles, or clothing online. Those transactions do not automatically turn the seller into a business owner, and the tax treatment depends partly on whether each item sold at a gain or a loss.

Suppose someone sells a used television for $150 after originally paying $500. The seller generally does not owe income tax on that personal sale because it produced a loss. However, the seller cannot deduct the $350 loss from other taxable income either. The reported payment may still require attention on the tax return to prevent the IRS from treating the gross amount as taxable income.

Now change the numbers. Someone buys a collectible for $200 and later sells it for $450. That $250 gain generally counts as a taxable capital gain, subject to the applicable rules. Selling several personal items can produce a mixture of gains and losses, so lumping every payment together can lead to the wrong result.

The distinction becomes more complicated if someone regularly buys goods specifically to resell for profit. That activity may constitute a business rather than occasional sales of personal belongings. Purchase records, selling patterns, and the purpose behind the transactions help establish the appropriate treatment.

A Missing 1099-K Does Not Make Income Tax-Free

Some side hustlers assume they can ignore earnings if a platform never sends a tax form. That assumption can create problems at filing time because tax-reporting obligations and information-reporting thresholds serve different purposes.

Under current IRS guidance, third-party payment networks generally must issue Form 1099-K when a recipient’s payments exceed $20,000 and involve more than 200 transactions. Payment card processors follow different reporting rules, and platforms may issue forms below the threshold. Those rules determine when certain organizations must report payments, not whether the recipient owes tax.

A dog walker who receives payments directly from customers, for instance, still needs to account for taxable business income even if no payment platform reports those earnings. The same principle applies to freelance designers, tutors, repair workers, and other independent earners.

Keep records of income from every source, not just amounts that appear on tax forms. If several platforms send separate 1099-Ks, reconcile each one against the underlying transactions. Otherwise, you could accidentally count the same earnings twice or overlook payments that no platform reported.

Your Tax Bill Depends on More Than Business Profit

Calculating net profit provides a starting point, but it does not settle the entire tax bill. A profitable side hustle can affect federal income tax and, for qualifying self-employed individuals, Social Security and Medicare taxes through the self-employment tax system. Your other income, deductions, filing status, and applicable tax rules also influence the final calculation.

For eligible self-employed individuals, net earnings from self-employment of $400 or more generally trigger a filing requirement for self-employment tax. Other filing requirements may apply even below that amount. Someone with a regular job and a weekend photography business may therefore face a different overall tax result from someone who relies entirely on freelance work.

Timing also deserves attention. Side-hustle income does not necessarily arrive in neat installments that line up with annual tax filing. Depending on the circumstances, estimated tax payments may help cover income and self-employment taxes throughout the year. Waiting until filing season to examine the numbers can leave a freelancer scrambling to cover a bill that accumulated over several months.

There is no reliable way to calculate the final amount owed from a 1099-K alone. The form does not account for every deduction, other income source, or personal tax circumstance. Treating its gross figure as the tax bill makes just as little sense as assuming that no form means no tax obligation.

Build a Paper Trail Before Tax Season Arrives

A simple recordkeeping routine can prevent hours of detective work later. Download transaction histories from payment platforms, save receipts for business purchases, and track refunds, fees, and shipping costs as they occur. If you sell personal belongings, retain purchase information when available so you can establish whether a sale generated a gain or loss.

Check every 1099-K for incorrect amounts, duplicate reporting, or transactions that belong to someone else. If the form contains errors, contact the issuer to request a correction and keep supporting documentation. When a payment total includes transactions for different activities, organize the amounts by their proper tax treatment rather than forcing everything into one category.

A tax professional may help when business and personal transactions overlap, resale activity becomes regular, or several forms report complicated payment streams. The goal is not to make every small side hustle complicated. It is to keep enough information to report the activity accurately and explain the numbers if questions arise.

Let the Transactions Tell the Tax Story

A 1099-K is a reporting document, not a verdict on how much money you made or how much tax you owe. Your actual tax picture emerges from the transactions behind that number, the expenses you can substantiate, and the rules that apply to your particular activities.

That distinction matters whether your side hustle brings in a few hundred dollars or becomes a substantial second income. Track the money, separate business activity from personal sales, and avoid confusing gross payments with profit. A little organization during the year can make tax season far less confusing.

Have you received a 1099-K for side-hustle income or selling personal belongings, and did the reported amount match what you actually earned? Share your experience in the comments.

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Brandon Marcus
Brandon Marcus

Brandon Marcus is a writer who has been sharing the written word since a very young age. His interests include sports, history, pop culture, and so much more. When he isn’t writing, he spends his time jogging, drinking coffee, or attempting to read a long book he may never complete.

Filed Under: Lifestyle Tagged With: 1099-K, gig economy, IRS, Personal Finance, self-employment income, side hustle taxes, Small business, Tax Deductions

The IRS October 15 Deadline Is Getting Close: 7 Things Extension Filers Should Do Now

September 30, 2026 by Brandon Marcus Leave a Comment

The IRS October 15 Deadline Is Getting Close: 7 Things Extension Filers Should Do Now
An IRS tax extension gives eligible taxpayers until October 15, 2026, to file their federal return, but it does not extend the deadline for paying taxes owed – Shutterstock

The IRS October 15 deadline for 2025 federal tax returns is getting close. For taxpayers who requested an extension, this is the point where waiting can turn a manageable filing into a frantic scramble.

An extension bought extra time to file, not extra time to pay. That distinction matters, especially for anyone who still has an unpaid balance from April. With the deadline approaching, a quick review can uncover missing documents, forgotten payments, or tax forms that never made it into the folder.

1. Pull Together Every Tax Document

Start with the paperwork before opening the tax software. Look for W-2s, 1099s, brokerage statements, retirement documents, mortgage interest statements, charitable contribution records, and anything else tied to 2025 income or deductions.

The IRS also recommends gathering and reviewing tax documents before filing because complete records can help reduce errors and processing delays. Taxpayers can use an IRS Individual Online Account to access certain tax information and transcripts.

This step can catch an especially annoying problem: a form that arrived months ago but disappeared into a drawer, inbox, or pile of mail. Filing based on incomplete paperwork can create more work later.

2. Check Whether the April Payment Actually Happened

An extension does not erase an April tax bill. The IRS required most calendar-year taxpayers to pay taxes due by April 15, even if they received an extension to file until October 15.

Before the return calculates a balance, check bank records and IRS account information for payments already made. Include estimated tax payments and any amount paid with the extension request. Forgetting a payment can make a tax bill look larger than it actually is.

If money remains due, paying as much as possible can limit additional interest and penalties. The IRS also offers payment options for taxpayers who cannot pay the entire balance.

3. Revisit the Parts of Life that Changed

Tax returns can change because life changed. A move, marriage, divorce, new child, retirement, job change, home purchase, investment sale, or side business can affect the information that belongs on the return.

That makes the extension period more than a pause button. It gives filers time to ask whether the tax return still reflects what actually happened during 2025.

Do not assume the information from an earlier draft remains correct. If income changed, a form arrived late, or a transaction received a corrected tax document, the return needs to reflect the updated information.

4. Look Closely at Credits and Deductions

A rushed return can overlook tax benefits just as easily as it can overlook income. The IRS notes that Free File’s guided software can help eligible taxpayers determine whether they qualify for certain credits, including the Earned Income Tax Credit and Child and Dependent Care Credit. That does not mean every taxpayer qualifies for every credit. Eligibility depends on the specific facts of the return, and some deductions require supporting records.

This is also a good reason to review rather than simply hit “submit” on an old draft. The goal should not be finding a magical deduction. It should be making sure legitimate items do not disappear because the filing process became a race against the calendar.

5. Decide How The Return Will Get Filed

There is still time to file electronically, and the IRS encourages extension filers to avoid waiting until October 15. IRS Free File remains available through October 15, 2026. Taxpayers with 2025 adjusted gross income of $89,000 or less may qualify for guided Free File software.

Taxpayers above that income threshold can use Free File Fillable Forms if they feel comfortable preparing their own return. Eligible military taxpayers also have access to MilTax.

Choosing the filing method now removes one more decision from the final week. It also leaves room to solve a software, document, or account-access problem before the deadline.

6. Do Not Forget the State Return

Federal and state tax deadlines can overlap, but they do not always operate under identical rules. A federal extension does not automatically answer every question about a state return.

Check the state revenue agency’s rules for the state where the return belongs. The filing deadline, payment requirements, extension process, and available options can differ.

That check matters even if the federal return looks finished. A taxpayer can have a federal filing ready to go while a separate state obligation still needs attention.

7. Give the Finished Return One Final Inspection

Before submitting, slow down for the least glamorous part of the process: reviewing the return. Check names, Social Security numbers, bank information, income figures, withholding, estimated payments, and major deductions or credits.

The IRS says taxpayers can file electronically through October 15 if they timely requested an extension. For 2026, the IRS lists October 15 as the final transmission date for returns filed on extension from Form 4868.

Do not wait until the final evening to discover that a document will not upload or a tax account password has vanished into the digital abyss. A few days of breathing room can make a surprisingly large difference.

October Is for Filing, Not Starting From Scratch

The smartest use of an extension is not to treat October 15 like a brand-new tax deadline. The deadline provides additional filing time, but unresolved tax payments, missing documents, and unanswered questions can still create problems.

October 15 may still look comfortably distant. It is not. The return does not need to be filed today, but it should be moving toward the finish line.

What part of filing an extended tax return tends to take the most time or cause the biggest headaches?

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Brandon Marcus
Brandon Marcus

Brandon Marcus is a writer who has been sharing the written word since a very young age. His interests include sports, history, pop culture, and so much more. When he isn’t writing, he spends his time jogging, drinking coffee, or attempting to read a long book he may never complete.

Filed Under: tax tips Tagged With: 2025 taxes, IRS, October 15 deadline, Personal Finance, tax deadline, tax extension, tax filing, tax tips, taxes

Roth Contributions in Your Peak Earning Years: The Bracket Math That Can Cost You Thousands in Retirement

September 29, 2026 by Brandon Marcus Leave a Comment

Roth Contributions in Your Peak Earning Years: The Bracket Math That Can Cost You Thousands in Retirement
A Roth contribution trades a current-year tax deduction for the possibility of tax-free qualified withdrawals later, making today’s tax bracket an important part of the decision – Shutterstock

Roth contributions can make retirement income tax-free, but that benefit comes with a price today. During peak earning years, that price can land in a much higher federal tax bracket than the one that applies after leaving work.

That makes the Roth decision less about picking a universally superior account and more about comparing two tax bills separated by decades. For a high earner, the difference between paying tax now and claiming a deduction today can reach thousands of dollars.

The Tax Bracket Matters More Than the Roth Label

A Roth 401(k) contribution does not reduce taxable income. A traditional 401(k) contribution generally does. That distinction can become expensive when a worker earns enough to sit near the upper end of a federal bracket.

For 2026, a single filer reaches the 32% marginal bracket once taxable income exceeds $201,775. The 24% bracket runs above $105,700 through $201,775. For married couples filing jointly, the 32% bracket begins above $403,550, while the 24% bracket extends through $403,550.

Think about a single worker with $210,000 of taxable income before a retirement contribution. A $10,000 traditional 401(k) contribution could pull taxable income down to $200,000. That does not mean the entire $10,000 saves 32%. The first $8,225 falls out of the 32% bracket, while the remaining $1,775 receives a 24% tax benefit.

That produces a federal tax reduction of roughly $3,048, before considering other factors. A Roth contribution of the same $10,000 would not provide that current-year deduction. The tax savings could instead remain invested, used for another financial goal, or simply reduce the household’s tax bill.

A Roth Can Still Win Later

The other side of the calculation arrives decades later. Qualified Roth 401(k) distributions generally can come out tax-free, provided the applicable requirements get met. Traditional 401(k) money generally faces ordinary income tax when withdrawn. That creates a straightforward question: Will the tax rate avoided today exceed the tax rate paid later?

Suppose someone gives up a 32% deduction during peak earning years and eventually withdraws traditional retirement money while paying an effective marginal rate closer to 22%. The tax rates do not match. Paying 22% later can cost less than paying 32% today.

That does not guarantee a traditional account will produce the better result. Retirement income can come from several sources, and tax brackets depend on the entire household tax return. Social Security benefits, pensions, investment income, traditional retirement withdrawals, charitable giving, filing status, deductions, and future tax law can all affect the calculation.

The Roth option also has a valuable feature beyond the tax rate itself. Tax-free qualified withdrawals can give retirees more control over taxable income. That flexibility can matter during years with unusually high income or large financial transactions.

The Biggest Mistake Happens at the Bracket’s Edge

A worker does not need to choose between “all Roth” and “all traditional.” Employer plans often allow employees to divide contributions between traditional and Roth accounts. That creates an opportunity to look at the actual tax return instead of treating retirement contributions like a philosophical choice. Someone near the top of a tax bracket could direct enough money into a traditional account to reduce income that falls into the higher bracket, then use Roth contributions for additional retirement savings.

The exact split depends on the household’s numbers. A person earning substantially more than the 32% threshold faces a different calculation than someone whose income barely crosses it. A married couple also gets different bracket thresholds from a single filer.

This is where a paycheck contribution can become more interesting than it first appears. The contribution percentage on the benefits website might look like a simple savings choice, but the tax treatment changes the amount of money available to the government today.

High Earners Also Need to Watch the Roth IRA Rules

The word “Roth” can describe several different accounts, and that distinction matters. For 2026, the combined annual contribution limit for traditional and Roth IRAs is $7,500, or $8,600 for someone age 50 or older. Roth IRA contributions also face income phaseouts. For single filers, the 2026 phaseout begins at $153,000 of modified adjusted gross income and ends at $168,000. For married couples filing jointly, the phaseout runs from $242,000 to $252,000.

A workplace Roth 401(k) works differently. The 2026 employee contribution limit for a 401(k) is $24,500, with additional catch-up contributions available for eligible older workers.

That difference matters for someone in peak earning years. A worker may earn too much for a direct Roth IRA contribution while still having access to a Roth 401(k) through an employer plan.

One 2026 Rule Changes the Catch-Up Calculation

Workers approaching retirement have another wrinkle to consider. Beginning in 2026, certain higher-paid employees must make catch-up contributions on a Roth basis if their prior-year wages from the employer exceeded $150,000. The rule applies to the catch-up portion, not the regular 401(k) deferral. For 2026, the standard catch-up limit generally reaches $8,000, while workers ages 60 through 63 can qualify for the higher $11,250 limit.

That means a high earner cannot necessarily choose traditional treatment for every dollar contributed to a 401(k). The plan’s rules and the employee’s prior-year wages can determine how the catch-up portion gets treated.

It also makes payroll planning more relevant for workers in their highest-income years. A person approaching retirement may face a different Roth-versus-traditional decision for regular contributions than for catch-up dollars.

The Better Question Is “Which Tax Year Gets the Money?”

Retirement planning often focuses on how much someone saves. Tax planning adds another question: Which tax year should absorb the tax?

Paying tax during a high-income year can make a Roth contribution less attractive when a traditional contribution would produce a valuable deduction. On the other hand, deliberately building Roth assets during years with unusually low income can create a very different calculation.

The most useful comparison starts with the marginal tax rate on the next dollar earned, then looks at how retirement withdrawals may interact with the rest of the household’s income. A spreadsheet that compares those two tax environments can reveal a very different picture from simply choosing whichever account has the more appealing name.

How are you balancing Roth and traditional retirement contributions during your highest-earning years?

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Brandon Marcus
Brandon Marcus

Brandon Marcus is a writer who has been sharing the written word since a very young age. His interests include sports, history, pop culture, and so much more. When he isn’t writing, he spends his time jogging, drinking coffee, or attempting to read a long book he may never complete.

Filed Under: Retirement Tagged With: 2026 taxes, IRS, Personal Finance, retirement planning, retirement taxes, Roth 401k, tax brackets, traditional 401(k)

The IRS Just Eased 401(k)-to-IRA Rollovers — But One Missed Step Still Costs You 20% Upfront

September 24, 2026 by Brandon Marcus Leave a Comment

The IRS Just Eased 401(k)-to-IRA Rollovers — But One Missed Step Still Costs You 20% Upfront
A direct 401(k)-to-IRA rollover generally avoids the mandatory 20% federal withholding that applies when an eligible taxable distribution goes directly to the participant – Shutterstock

The IRS just moved to make 401(k)-to-IRA rollovers easier to handle, but the old 20% withholding rule still matters. A new IRS notice gives retirement plans sample forms and proposed procedures for direct rollovers, aiming to make the process more standardized and less confusing.

That change does not eliminate the biggest trap in the process. If a taxable 401(k) distribution comes directly to you instead of going straight to the IRA, the plan generally must withhold 20% for federal taxes.

That creates a peculiar situation: The money can still qualify for a tax-deferred rollover, but the check can arrive short by one-fifth.

The IRS Changed the Paperwork, Not the 20% Rule

On Aug. 12, 2026, the Treasury Department and IRS released Notice 2026-49 with sample forms and proposed procedures for direct rollovers. The guidance responds to Section 324 of the SECURE 2.0 Act and covers rollovers between retirement plans and between a retirement plan and an IRA.

The IRS designed the sample forms to reduce paperwork and protect personal identifying information. Plans can use them, but the forms remain optional because the IRS has proposed procedures rather than imposing a universal new process.

So the practical change looks less dramatic than the headline might suggest. The IRS wants the handoff between accounts to become cleaner and more standardized, but it did not rewrite the basic tax treatment of a 401(k) distribution paid to you.

That distinction matters because someone moving an old workplace account may see “rollover” and assume every method works the same way. They do not.

The Safest-Looking Check Can Create a Cash Problem

A direct rollover keeps the money moving from the old retirement plan to the new IRA without the distribution passing through your hands. The IRS says a direct rollover does not trigger federal tax withholding.

A different process applies if the plan sends the distribution to you. For most eligible taxable rollover distributions, the payer must withhold 20% for federal income taxes, even when you tell the plan that you intend to roll the money into an IRA.

Consider a simple $50,000 distribution. A plan could withhold $10,000 and send you $40,000. You can still complete a 60-day rollover, but the IRS generally requires you to replace that $10,000 with other money if you want the entire $50,000 treated as a rollover. The IRS specifically explains that the withheld amount counts as part of the distribution, so leaving it out can make that portion taxable.

That creates a frustrating cash-flow problem. The money technically belongs to the retirement distribution, yet the taxpayer may need separate cash to put the full amount back into retirement savings.

Sixty Days Sounds Generous until The Check Sits on A Desk

A payment made directly to you generally gives you 60 days to complete the rollover. The clock starts with the date you receive the distribution. That sounds manageable, and often it is. But the 60-day window does not turn a personal check into a direct rollover.

Suppose someone leaves an employer, requests a 401(k) distribution and plans to open an IRA afterward. The check arrives, then a weekend disappears, an account application takes longer than expected, and suddenly the rollover becomes a deadline rather than a simple transfer.

The cleaner approach involves setting up the receiving IRA first and asking the former employer’s plan administrator about its direct-rollover procedure. The receiving institution can provide instructions for where the money should go and how the check should list the recipient.

The IRS also notes that a plan can send a check payable to the receiving plan or IRA without triggering the 20% withholding that applies when the payment goes directly to the participant. (IRS)

That tiny difference in how a check gets addressed can have a very real tax consequence.

A Rollover and A Roth Conversion Are Not the Same Move

Another wrinkle deserves attention before anyone treats “IRA rollover” as a synonym for “tax-free.”

Moving pre-tax 401(k) money into a traditional IRA generally preserves tax deferral when the transaction qualifies as a rollover. The IRS says the taxable amount generally does not enter income until a later distribution.

Moving pre-tax 401(k) money into a Roth IRA works differently. A Roth conversion generally creates taxable income because the taxpayer moves money from a pre-tax account into an account with different tax treatment.

The withholding issue can still matter during a Roth conversion. If the plan pays the money to the participant, the mandatory 20% withholding can reduce the amount available for the conversion unless the taxpayer supplies additional funds.

The 20% Is Withholding, Not Necessarily the Final Tax Bill

Seeing 20% disappear from a retirement distribution can make the transaction look like an automatic 20% tax. That is not quite what happened.

The IRS treats the withheld amount as federal income tax paid on the distribution. If the taxpayer completes a full rollover and replaces the withheld amount from other funds, the entire eligible distribution can generally remain tax-deferred.

If the taxpayer rolls over only the amount that actually arrived, the withheld portion may become taxable. Someone under 59½ could also face the 10% additional tax on the taxable amount unless an exception applies.

The distinction matters at tax time because withholding and actual tax liability serve different purposes. The withholding represents money sent toward the tax bill. It does not automatically mean the taxpayer ultimately owes that exact percentage on the distribution.

A Smoother Rollover Still Starts with One Careful Question

The new IRS guidance could make direct rollovers easier for plans and participants, but the mechanics still deserve attention. Notice 2026-49 does not erase the 20% withholding rule for eligible taxable retirement-plan distributions paid to participants.

Before requesting a distribution, a retirement saver can ask the plan administrator a very specific question: Will this payment go directly to the receiving IRA, or will the check come to me? That question can prevent a surprisingly expensive paperwork detour.

For anyone moving an old 401(k), the difference between “payable to the IRA” and “payable to me” can matter more than the size of the check itself. A cleaner process may be arriving, but the old rule still rewards careful attention before the money leaves the retirement plan.

Would you choose a direct rollover after seeing how the 20% withholding rule works, or would you consider another option for an old 401(k)? Share your thoughts in the comments.

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Brandon Marcus
Brandon Marcus

Brandon Marcus is a writer who has been sharing the written word since a very young age. His interests include sports, history, pop culture, and so much more. When he isn’t writing, he spends his time jogging, drinking coffee, or attempting to read a long book he may never complete.

Filed Under: Retirement Tagged With: 401(k), IRA, IRS, Personal Finance, Retirement, retirement planning, rollovers, taxes

IRS Gives Drought-Hit Farmers and Ranchers More Time to Replace Livestock and Defer Taxes

September 22, 2026 by Amanda Blankenship Leave a Comment

IRS drought livestock tax relief
The IRS has extended tax relief for eligible farmers and ranchers who were forced to sell qualifying livestock because of drought. Notice 2026-54 identifies affected areas in 49 states, the District of Columbia, Puerto Rico and other regions and can give qualifying producers additional time to replace livestock while deferring certain gains from drought-related sales. Nicole Dennis/Shutterstock

Farmers and ranchers who were forced to sell livestock because of drought may have additional time to replace those animals without immediately recognizing certain gains for federal tax purposes.

The Internal Revenue Service announced the extension on September 15, 2026. The relief covers qualifying areas in 49 states, the District of Columbia, Puerto Rico and other regions that experienced exceptional, extreme or severe drought during the 12-month period ending August 31, 2026.

“Large swaths of the United States continue to experience drought conditions, distressing hard-working American farmers and ranchers,” IRS Chief Executive Officer Frank J. Bisignano said in announcing the relief.

The rules can give qualifying agricultural producers additional time to replace livestock sold because of drought while allowing them to defer recognition of certain gains from those forced sales or exchanges.

Who Can Qualify for the Livestock Tax Relief?

The relief doesn’t apply to every livestock sale made by a farmer or rancher in one of the 49 states.

Under IRS Notice 2026-54, the rules generally concern livestock held for draft, breeding or dairy purposes that were sold or exchanged because of qualifying drought conditions.

The tax treatment stems from Internal Revenue Code Section 1033, which provides rules for certain involuntary conversions. For livestock, qualifying sales or exchanges can receive special treatment when animals are sold solely because of drought, flooding or another weather-related condition that results in the area being designated as eligible for federal assistance.

Livestock raised for slaughter doesn’t qualify under these particular provisions. Poultry and livestock held for sporting purposes are also excluded.

Farmers and ranchers must be able to establish that the drought caused the qualifying sale or exchange.

The Normal Replacement Period Can Grow From Two Years to Four

Timing is one of the most important parts of the tax provision.

The normal replacement period for an involuntary conversion is generally two years, but qualifying livestock sales caused by drought or other specified weather-related conditions can receive a four-year replacement period.

The IRS can extend that four-year period even further on a regional basis when the drought conditions persist.

Notice 2026-54 specifically addresses farmers and ranchers whose four-year drought-sale replacement period was scheduled to expire at the end of 2026—or, for certain fiscal-year taxpayers, during the taxable year that includes August 31, 2026.

When the applicable region continues to meet the drought conditions described by the IRS, the replacement period can continue until the end of the taxpayer’s first tax year ending after the first drought-free year for that region.

That distinction is important: the IRS isn’t simply handing every producer a new four-year deadline beginning in 2026.

Qualifying Areas Are Determined County by County

Although the IRS announcement says the latest relief reaches areas in 49 states, eligibility isn’t necessarily statewide.

Notice 2026-54 contains an extensive appendix identifying counties and other jurisdictions where exceptional, extreme or severe drought was reported during the 12 months ending August 31, 2026.

For purposes of the extension, the applicable region includes the county where the drought-related livestock sale occurred as well as counties contiguous to that county.

The IRS relies on weekly U.S. Drought Monitor information produced by the National Drought Mitigation Center. For this latest extension, qualifying drought conditions had to be reported during at least one week between September 1, 2025, and August 31, 2026.

Farmers shouldn’t assume they’re covered merely because their state appears on the IRS’s 49-state list. Checking the specific county or other jurisdiction listed in the notice is an important first step.

Why the Extension Can Matter Financially

Forced livestock sales can create a difficult tax problem for agricultural producers already dealing with drought.

A rancher may need to reduce a breeding herd because there isn’t enough pasture, forage or water to maintain the animals. Selling those animals can produce taxable gain even though the sale wasn’t part of the producer’s normal business plan.

The special replacement rules can allow an eligible producer to defer recognition of qualifying gain while giving the operation time to rebuild the herd after conditions improve.

That extra time can be particularly important when drought lasts for several consecutive years and replacing livestock immediately would be impractical or financially difficult.

The rules are detailed, however, and not every livestock sale receives the same tax treatment. Farmers and ranchers dealing with significant drought-related sales may want to work with a tax professional familiar with agricultural taxation before assuming a particular transaction qualifies.

Check Your County Before the Replacement Deadline Arrives

Farmers and ranchers who previously made qualifying drought-related livestock sales should review the new notice if their replacement period was approaching its deadline.

The IRS directs taxpayers to Notice 2006-82 for additional details and examples explaining how drought-related replacement-period extensions work.

Broader guidance on livestock sales, farming income and other agricultural tax issues is available in the IRS’s Publication 225, Farmer’s Tax Guide.

The key is not to assume that living in one of the 49 affected states automatically qualifies every livestock transaction for relief. Producers should confirm their location, why the livestock was sold, what the animals were used for, and when their existing replacement period would otherwise expire before relying on the extension.

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Headshot of Amanda Blankenship
Amanda Blankenship

Amanda Blankenship is the Chief Editor for District Media.  With a BA in journalism from Wingate University, she frequently writes for a handful of websites and loves to share her own personal finance story with others. When she isn’t typing away at her desk, she enjoys spending time with her daughter, son, husband, and dog. During her free time, you’re likely to find her with her nose in a book, hiking, or playing RPG video games.

Filed Under: news Tagged With: agriculture, drought, drought relief, farm taxes, farmers, IRS, livestock, Notice 2026-54, ranchers, tax relief

IRS Sets December Hearing on Proposed Tax-Exempt Rules for Racial Nondiscrimination at Private Schools

September 17, 2026 by Amanda Blankenship Leave a Comment

IRS private school tax exemption
Treasury and the IRS are proposing updated racial nondiscrimination requirements for tax-exempt private schools, with a public hearing scheduled for December 2. The agencies estimate the proposal could affect as many as 18,000 private educational institutions. Ground Picture/Shutterstock

The Internal Revenue Service has scheduled a December public hearing on proposed regulations that would update federal tax-exemption rules governing racial nondiscrimination at private schools.

The hearing is scheduled for December 2, 2026, at 10 a.m. Eastern Time and will take place entirely by teleconference. It follows proposed regulations issued earlier this month by the Treasury Department and IRS under REG-119986-25.

The proposal would provide that a private school does not qualify for federal tax-exempt status under Section 501(c)(3) if it adopts, maintains, or enforces a policy or practice that discriminates on the basis of race, color, or national or ethnic origin.

Private Schools Already Face Nondiscrimination Requirements

The proposal isn’t creating the concept of racial nondiscrimination as a condition of tax exemption from scratch.

Current IRS guidance for tax-exempt organizations says a private school seeking federal tax-exempt status must have a racially nondiscriminatory policy toward students and cannot discriminate against applicants or students based on race, color, or national or ethnic origin.

Existing requirements also address admissions, scholarships, loans, school programs and athletics. Tax-exempt private schools generally must publicize their nondiscrimination policies and maintain certain records demonstrating compliance.

The Treasury Department and IRS say the proposed regulations would update those rules in light of Supreme Court decisions and establish a uniform nondiscrimination standard.

The Proposal Would Also Address Race-Based Preferences

One significant part of the proposal involves provisions of existing IRS guidance that have allowed certain policies favoring racial minority groups when their purpose and effect were to establish or maintain a school’s nondiscriminatory policy.

Treasury and the IRS propose eliminating those provisions, saying the exceptions are inconsistent with the uniform nondiscrimination standard contemplated by the new regulations.

Under the proposal, covered schools couldn’t make admissions decisions or provide benefits based on race, color, or national or ethnic origin. Schools could continue programs intended to expand educational opportunity using race-neutral criteria such as family income, geographic location, first-generation status, individual hardship, military-family status, or academic achievement.

The proposal also wouldn’t prevent private schools from maintaining religious missions or programs. Treasury and the IRS say religious schools could continue selecting students based on genuine religious affiliation or membership when consistent with federal law.

The agencies estimate that the regulations could affect as many as 18,000 private educational institutions, including private primary and secondary schools, colleges, universities, professional schools and trade schools.

December 2 Hearing Will Be Conducted by Telephone

According to the federal hearing notice, anyone wishing to testify must submit an outline of the topics they plan to discuss by November 3, 2026.

Each speaker will receive 10 minutes.

If the IRS receives no outlines by November 3, the hearing will be cancelled, and the agency will publish a cancellation notice.

People who want to attend without testifying must register by email by November 30 to receive the telephone number and access code. Requests for disability-related assistance must be submitted by November 27.

Testimony outlines can be submitted through the federal rulemaking portal by identifying IRS and REG-119986-25 or mailed to the IRS address provided in the official notice.

The Rules Wouldn’t Take Effect Immediately

The proposal remains just that—a proposal. The hearing and public-comment process occur before Treasury, and the IRS determines what will appear in final regulations.

The September 4 proposed regulations state that the new rules, if finalized as contemplated, would affect private schools for taxable years beginning on or after May 31, 2027.

That distinction is important for schools, families, and donors because the September proposal hasn’t itself changed the current requirements for tax-exempt private schools.

For donors, a school’s federal tax-exempt status can also matter when determining whether a charitable contribution qualifies for a federal income-tax deduction, subject to the applicable tax rules.

The December hearing gives schools, nonprofit organizations and other interested parties another opportunity to weigh in before the regulations are finalized. Written comments on the underlying proposal and requests for a public hearing are also due November 3.

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Headshot of Amanda Blankenship
Amanda Blankenship

Amanda Blankenship is the Chief Editor for District Media.  With a BA in journalism from Wingate University, she frequently writes for a handful of websites and loves to share her own personal finance story with others. When she isn’t typing away at her desk, she enjoys spending time with her daughter, son, husband, and dog. During her free time, you’re likely to find her with her nose in a book, hiking, or playing RPG video games.

Filed Under: news Tagged With: 501(c)(3), charitable organizations, Education, Federal Regulations, IRS, nonprofit schools, private schools, tax rules, tax-exempt organizations, Treasury Department

IRS Proposes New Tax Rules for U.S. Companies With Foreign Income and Overseas Operations

September 14, 2026 by Amanda Blankenship Leave a Comment

IRS foreign tax credit rules
The IRS and Treasury Department are proposing new rules for allocating deductions when certain U.S. companies calculate foreign tax credits and deductions connected to foreign-derived income. DK_STUDIO29/Shutterstock

U.S. companies doing business overseas could face updated rules for calculating important international tax deductions and foreign tax credits under a new proposal from the Internal Revenue Service and Treasury Department.

The proposed regulations, published September 11, are intended to implement international tax changes Congress enacted in the 2025 One, Big, Beautiful Bill Act.

For most individual taxpayers, the proposal won’t change how they prepare their federal income tax returns. Instead, the rules primarily matter to domestic corporations claiming a deduction connected to foreign-derived income and taxpayers operating abroad through foreign corporations.

What Is the IRS Proposing?

At the center of the proposal is a complicated but important tax question: When a company has income from both U.S. and foreign sources, which expenses and deductions should be assigned to each?

That calculation matters because assigning a deduction to one category of income rather than another can change the amount of income used to calculate certain tax benefits.

The proposed regulations address two areas.

The first involves the calculation of deduction eligible income, or DEI, used in determining a domestic corporation’s deduction for foreign-derived deduction eligible income, commonly abbreviated FDDEI.

The second involves the foreign tax credit limitation for foreign-source Section 951A category income. That category generally relates to income U.S. shareholders recognize from controlled foreign corporations.

The IRS proposal provides detailed rules for deciding how deductions should be allocated and apportioned when companies make those calculations.

The Rules Stem From the 2025 Tax Law

Congress changed both areas as part of the One, Big, Beautiful Bill Act, which was signed into law July 4, 2025.

The changes generally apply to taxable years beginning after December 31, 2025.

For deduction eligible income, the amended law changed which deductions reduce gross income when calculating DEI.

Under the new framework, deductions—including certain taxes—that are properly allocable to the relevant gross income generally reduce DEI. However, interest expense and research or experimental expenditures are excluded from that reduction.

The proposed Treasury regulations provide instructions for applying those statutory changes.

Foreign Tax Credit Calculations Are Changing Too

The foreign tax credit is designed, broadly speaking, to reduce the potential for U.S. taxpayers to be taxed twice on qualifying foreign income.

But determining how much foreign tax credit a taxpayer can use involves a limitation calculation, and that requires determining how much taxable income belongs in different foreign-income categories.

The 2025 law added special rules under Section 904(b)(5) for deductions associated with foreign-source Section 951A category income.

Under those rules, certain deductions—including the Section 250 deduction associated with net CFC tested income and certain taxes—are allocated to that foreign-source income.

Interest expenses and research and experimental expenditures, meanwhile, aren’t allocated to foreign-source Section 951A category income under the new rules.

Other deductions generally go to that foreign-source category only when they are directly allocable to it. Otherwise, they’re allocated to U.S.-source income.

The proposed regulations provide additional details for putting those rules into practice.

Who Actually Needs to Pay Attention?

This isn’t a proposal that the typical employee, retiree or small household needs to factor into a Form 1040.

Treasury and the IRS say the regulations would primarily affect taxpayers operating in foreign countries through foreign corporations and domestic corporations claiming the deduction for foreign-derived deduction eligible income.

That means companies with foreign subsidiaries, significant international operations or qualifying foreign-derived income—and the tax professionals advising them—have much more reason to study the proposal closely.

The allocation rules can affect both the amount of income used in calculating the FDDEI deduction and the limitation on foreign tax credits.

Because international corporate tax calculations can involve multiple entities, income categories and jurisdictions, affected businesses should evaluate the proposal based on their particular structures rather than relying on a simplified example.

Companies May Be Able to Use the Proposed Rules Before They’re Final

One noteworthy part of the proposal is that affected taxpayers don’t necessarily have to wait for Treasury to publish final regulations before relying on the new guidance.

The proposed rules generally apply to taxable years beginning after December 31, 2025.

Treasury and the IRS also say taxpayers may rely on the proposed Section 250 rules before final regulations are published if they follow the applicable proposed regulations in their entirety.

Similar reliance is available for the proposed rules addressing Section 904(b)(5) and related deduction allocation, again provided taxpayers follow those proposed provisions in their entirety.

That can give businesses and their tax advisers a framework for dealing with the statutory changes while the formal rulemaking process continues.

IRS Wants Comments by November 10

These regulations aren’t final yet.

The IRS is accepting written and electronic comments on the proposal, along with requests for a public hearing, through November 10, 2026.

Electronic comments can be submitted through the federal rulemaking portal by referencing REG-117273-25.

Treasury and the IRS will consider those comments before moving ahead with final regulations.

For most consumers, there is no immediate tax action required because of this proposal. Businesses with controlled foreign corporations, foreign-derived income or significant cross-border operations, however, may want their tax professionals to review the rules now because the underlying statutory changes already apply to taxable years beginning after December 31, 2025.

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Headshot of Amanda Blankenship
Amanda Blankenship

Amanda Blankenship is the Chief Editor for District Media.  With a BA in journalism from Wingate University, she frequently writes for a handful of websites and loves to share her own personal finance story with others. When she isn’t typing away at her desk, she enjoys spending time with her daughter, son, husband, and dog. During her free time, you’re likely to find her with her nose in a book, hiking, or playing RPG video games.

Filed Under: news Tagged With: Corporate Taxes, FDDEI, foreign income, foreign tax credit, international taxes, IRS, One Big Beautiful Bill Act, Section 951A, tax regulations, Treasury Department

September 15 Is a Major Tax Deadline – Who Actually Needs to Pay the IRS?

September 12, 2026 by Brandon Marcus Leave a Comment

September 15 Is a Major Tax Deadline - Who Actually Needs to Pay the IRS?
September 15, 2026, marks the third estimated federal tax payment deadline for many individuals, including taxpayers with self-employment or other income without sufficient withholding – Shutterstock

September 15 can sneak up on taxpayers because it does not involve the giant annual tax-day frenzy that surrounds April 15. Yet for millions of Americans, September 15 marks the deadline for the third estimated federal tax payment of 2026, and ignoring it could create an unpleasant surprise later.

The deadline generally matters to people who earn income without enough tax coming out of each paycheck, including many self-employed workers, investors and business owners. The good news? Plenty of taxpayers can happily leave September 15 alone.

September 15 Is Really About Estimated Taxes

The IRS divides estimated tax payments into four periods during the year, and September 15 marks the payment deadline for income earned from June 1 through August 31. For 2026, individuals generally use Form 1040-ES to calculate and pay the third installment of their estimated federal income tax.

Think of estimated taxes as the pay-as-you-go version of income taxes, rather than one giant bill waiting at the end of the year. Instead of having an employer automatically withhold enough money from every paycheck, certain taxpayers send money to the IRS during the year as they earn income.

Who Actually Needs to Send Money?

The September deadline can matter if income arrives without enough withholding attached to it, which commonly happens with self-employment income, investment income, taxable retirement income and some other types of non-wage earnings. The IRS generally says individuals, including sole proprietors, partners and S corporation shareholders, should make estimated payments when they expect to owe at least $1,000 when they file their return.

A freelancer who has a great summer and watches several large client payments land in a bank account, for example, may need to account for taxes during the year rather than waiting until filing season. The same issue can pop up for someone with substantial investment gains or other income that does not come with traditional paycheck withholding.

A Regular Paycheck Can Change the Picture

People who receive wages often have an easier path because employers generally withhold federal income tax from their paychecks. A taxpayer who realizes the withholding falls short can potentially increase withholding by submitting a new Form W-4 to the employer, which can reduce the need for separate estimated payments.

That does not mean every employee can forget about September 15, though, especially if a side business, investment activity or other income sits outside the paycheck. The IRS looks at the taxpayer’s overall tax situation, so a regular paycheck does not automatically provide a force field against estimated-tax requirements.

Some Taxpayers May Not Need a September Payment

A taxpayer generally does not have to make estimated payments for the current year if all three IRS conditions apply: the person had no tax liability in the prior year, held U.S. citizenship or resident-alien status for the entire year, and had a prior tax year covering 12 months.

Taxpayers who receive enough withholding throughout the year may also avoid separate estimated payments because withholding counts toward the tax they owe. The important detail involves the amount and timing of tax payments, because paying too little during the year can trigger an underpayment penalty even when the taxpayer eventually pays the full balance at filing time.

Missing the Deadline Can Cost More Than a Calendar Reminder

The IRS treats estimated taxes as part of its pay-as-you-go system, so missing or underpaying an installment can lead to an underpayment penalty. The size of any penalty depends on the taxpayer’s circumstances and payment history, which means a missed deadline does not automatically translate into one universal fee.

Someone who realizes September 15 slipped away should not toss the paperwork into a drawer and hope January brings better news. Making the payment as soon as possible can limit the period of underpayment, while taxpayers with more complicated situations may want to review their calculations or seek qualified tax help rather than guessing at the amount.

September 15 Has Other Tax Jobs, Too

Estimated payments do not represent the only tax business landing on September 15, because the IRS calendar also lists several filing and payment obligations for businesses and certain organizations. Calendar-year S corporations and partnerships that requested timely extensions generally face September 15 filing deadlines, while corporations also make their third estimated tax installment around this date.

That distinction matters because someone might hear “September 15 tax deadline” and assume every taxpayer needs to write the IRS a check. For many people, September 15 passes like any other Tuesday, while for others it represents an important checkpoint for keeping their 2026 federal tax bill on track.

Make September 15 a Checkpoint, Not a Tax Surprise

The smartest move involves looking at the entire 2026 tax picture before deciding whether a September payment belongs on the calendar. Review year-to-date income, withholding and previous estimated payments, then compare those figures with the tax liability expected for the full year. Form 1040-ES provides worksheets that taxpayers can use to calculate estimated payments, and the IRS also offers online payment options.

One more wrinkle deserves attention: taxpayers with fiscal years can follow different estimated-tax schedules, so the standard September 15 date does not cover every situation. For calendar-year taxpayers, however, September 15, 2026, is the third estimated-tax payment deadline, making it a date worth circling before the calendar gets buried under football schedules, school events and pumpkin-spice everything.

Does the September 15 tax deadline catch you every year, or do you have a system for keeping estimated payments under control? Share your experience in the comments.

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Brandon Marcus
Brandon Marcus

Brandon Marcus is a writer who has been sharing the written word since a very young age. His interests include sports, history, pop culture, and so much more. When he isn’t writing, he spends his time jogging, drinking coffee, or attempting to read a long book he may never complete.

Filed Under: tax tips Tagged With: 2026 taxes, Estimated taxes, IRS, quarterly taxes, self-employed, September 15 tax deadline, tax deadlines, tax payments

You Can Pay the IRS Directly From Your Bank Account for Free—No Registration Required

September 11, 2026 by Amanda Blankenship Leave a Comment

IRS Direct Pay
IRS Direct Pay allows taxpayers to send eligible federal tax payments directly from a checking or savings account without registering for an IRS Online Account or paying a Direct Pay fee. Users can make same-day payments or schedule them up to 365 days in advance and receive a confirmation number after submitting the request. BLACKDAY/Shutterstock

Paying a federal tax bill online doesn’t necessarily require creating another account—or paying a processing fee to use a credit or debit card.

The Internal Revenue Service issued a reminder September 10 that its Direct Pay service allows taxpayers to send federal tax payments directly from a checking or savings account for free. No registration or IRS Online Account is required.

The tool can be useful for taxpayers paying a balance due, making estimated tax payments, paying after filing an amended return, requesting certain filing extensions, or handling several other federal tax obligations.

Here’s what taxpayers should know before using it.

Direct Pay Doesn’t Require an IRS Account

IRS Direct Pay works differently from the agency’s Individual Online Account.

Taxpayers using Direct Pay make a one-time payment without signing in or registering for an account. Individual taxpayers instead answer identity-verification questions using information from a prior-year tax return they select.

For businesses, the system verifies the business name and employer identification number against IRS records.

Payments are made directly from a checking or savings account at a U.S. financial institution using the bank’s routing and account numbers.

The IRS describes Direct Pay as both free and secure.

You Can Use It for More Than a Tax Bill

Direct Pay isn’t limited to paying the balance shown on an annual income tax return.

Individual taxpayers can use it for numerous payment types, including balance-due payments, estimated taxes, amended returns, installment agreements and certain extension payments.

Business taxpayers can use Direct Pay for balance-due payments, federal tax deposits and other eligible federal tax payments.

There is an important rule for married couples filing jointly: taxpayers generally need to enter information for the spouse whose name appears first on the joint tax return when making the payment.

The IRS provides a list of eligible payment types through its Direct Pay Help resources.

Payments Can Be Scheduled Up to a Year Ahead

Direct Pay also offers some flexibility for people who don’t want the money withdrawn immediately.

The IRS says taxpayers can make a same-day payment or schedule one as far as 365 days in advance. That could be particularly useful for someone planning estimated tax payments or preparing ahead for a known tax deadline.

After submitting a payment request, taxpayers receive a confirmation number and can also choose to receive confirmation by email.

Keep that number.

It is needed if you later want to look up, change, or cancel the payment. The IRS generally allows a scheduled Direct Pay payment to be changed or canceled up to two business days before its scheduled date.

One limitation is that Direct Pay handles one payment at a time rather than establishing an automatic recurring-payment schedule.

There Are Several Important Limits

Direct Pay isn’t available for every taxpayer or every situation.

People who have never filed a federal tax return—or who haven’t filed one in more than six years—may need to choose another IRS payment method because Direct Pay relies on prior return information for individual identity verification.

The service also cannot be used to have a tax refund directly deposited into your bank account. Despite the similar terminology, Direct Pay is a payment service for sending money to the IRS, not receiving a refund from it.

The IRS also limits users to five Direct Pay payments within a 24-hour period.

Individual Direct Pay payments must be less than $10 million. Taxpayers needing to make a payment of $10 million or more can use a same-day wire transfer or the Electronic Federal Tax Payment System when eligible and enrolled.

Don’t Stop at the Confirmation Screen

Receiving a Direct Pay confirmation number means the IRS received the payment request, but taxpayers should still make sure the money was successfully withdrawn.

The IRS recommends checking your bank statement or IRS account at least 48 hours after the requested payment date to confirm the transaction was completed.

That’s particularly important because a payment request could fail if, for example, the account doesn’t contain enough money to cover the withdrawal.

Saving the confirmation number and checking the corresponding bank transaction gives taxpayers documentation if they later need to investigate a payment problem.

Start at IRS.gov Instead of a Search Ad or Unfamiliar Link

Taxpayers interested in Direct Pay should access it through IRS.gov rather than relying on an unsolicited email, text message, advertisement, or unfamiliar website claiming to collect federal tax payments.

The legitimate IRS tool does not charge taxpayers a fee to send an eligible payment directly from their checking or savings account.

That’s an important distinction from some other electronic payment options. The IRS notes that taxpayers who choose to pay federal taxes using a debit card, credit card, or digital wallet generally make the transaction through an approved payment processor that charges a processing fee.

For someone who simply wants to send money directly from a bank account without registering for another online service, Direct Pay provides a relatively straightforward alternative.

Just verify the payment type, bank information, tax year, and amount carefully before submitting—and save the confirmation number until you’re certain the payment has been processed.

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Headshot of Amanda Blankenship
Amanda Blankenship

Amanda Blankenship is the Chief Editor for District Media.  With a BA in journalism from Wingate University, she frequently writes for a handful of websites and loves to share her own personal finance story with others. When she isn’t typing away at her desk, she enjoys spending time with her daughter, son, husband, and dog. During her free time, you’re likely to find her with her nose in a book, hiking, or playing RPG video games.

Filed Under: news Tagged With: Estimated taxes, federal taxes, income taxes, IRS, IRS Direct Pay, IRS payments, Personal Finance, tax payments, tax tips, Taxpayers

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