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Top 5 Mistakes That Trigger IRS Audits (And How to Avoid Costly Tax Debt)
IRS Audits Are Not Random — They Are Triggered Many taxpayers believe IRS audits are rare or purely random. In reality, most audits are the result of automated data-matching systems that flag inconsistencies, statistical anomalies, or high-risk patterns. The IRS compares what you report on your return against what employers, banks, brokers, payment platforms, and…
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Tax Document Checklist: Don’t Miss These (Or Risk IRS Problems Later)
Filing Without the Right Documents Is One of the Fastest Ways to Create Tax Debt Every year, thousands of taxpayers across the United States receive unexpected IRS notices — not because they intended to underreport income, but because they missed a form. The IRS receives copies of most income documents issued under your Social Security…
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S-Corp & Partnership Filers: Avoid These Last-Minute Errors Before They Trigger IRS Problems
Business Entity Tax Filings Carry Higher Stakes Than Most Owners Realize If you operate as an S-Corporation or partnership, your tax return is more than a formality — it is the foundation for your personal tax reporting, shareholder compliance, and IRS scrutiny. Unlike individual returns, S-Corp and partnership filings generate pass-through documentation (Schedule K-1) that…
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Missed an Estimated Tax Payment? Here’s What to Do (Before It Gets Worse)
If you’re self-employed and just realized you missed an estimated tax payment, take a breath. You’re not the first business owner this has happened to—and you won’t be the last. At Tax Workout Group, we regularly speak with freelancers, consultants, contractors, and small business owners who meant to send in their quarterly payment… but life,…
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2026 Tax Survival Guide: What to Do Now to Stay Out of Trouble
If you’ve ever seen an envelope from the IRS and thought, “I’m going to open this later,” you’re not alone. At Tax Workout Group, we talk to taxpayers every day who feel anxious, overwhelmed, or unsure whether they’ve already made a mistake. As we head into 2026, those concerns are understandable. Tax rules continue to…
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Should You Consider Chapter 13 Bankruptcy Instead of an IRS Payment Plan?
Now that April 15th has come and gone, millions of Americans have exhaled a collective sigh of relief — unless, of course, you still owe the IRS. If you’re one of the unlucky taxpayers now staring down a balance due (and perhaps a love letter from the IRS marked “Final Notice of Intent to Levy”),…
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The Tax Survival Arsenal — for When the IRS Comes Knocking, and Before
I doubt if many people associate good dreams with the IRS. Nightmares, maybe, but in any event not the kind of thoughts to take into Z-Land. And not the kind of thoughts to wake up to either. Come to think of it, I don’t believe there is any good time for thoughts like that. I…
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When the IRS Gets Six Years Instead of Three – The Tax Time Bomb You’ve Never Heard Of: §6501(e)(1)(A)(i)
§6501(e)(1)(a)(i)—I first heard of this section of the Internal Revenue Code in one of my initial classes at NYU in the program for an LL.M. in Tax (Masters in Tax Law). The professor who said it had no notes in front of him, no monitor, no nothing. I thought he was making some kind of…
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The IRS “Fresh Start” Program: It Doesn’t Exist
There is not now and there never has been an IRS Fresh Start Program. None. Nada. If anyone tells you different, they’re selling false hopes of utopia and you’re the prospective payor. Let’s start with a bit of background. The IRS started using the optimistic and somewhat friendly sounding catchphrase “Fresh Start” with a brief…
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IRS Certified “Collection Notices” – A Complete 2025 Guide
If you’re expecting to see a listing and detailed description of every kind of certified mail that the IRS might ever send, well, consider yourself saved. The primary and most important consideration is that if a professional has not been consulted prior to receipt of a certified letter on any particular matter or issue, the…
