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  Is Your "Tax Debt" Weighing You Down? Why 2026 is the Year to Clean the Slate If you have unfiled tax returns from 2023, 2024, or earlier, it’s easy to feel like the safest move is to stay under the radar. But in the current 2026 tax landscape, the opposite is true. Between new IRS technology and the permanent shifts from the One Big Beautiful Bill Act (OBBBA) , the "wait and see" strategy is becoming increasingly expensive. Here is why now is the absolute best time to get caught up: 1. The "Statute of Limitations" Clock is Ticking You generally only have a three-year window from the original due date to claim a tax refund. If you didn't file for 2022, you are approaching the final deadline to claim any money the government owes you. Once that window closes, that money belongs to the IRS forever. 2. New IRS "Digital Eyes" In 2026, the IRS has fully deployed its advanced AI data-matching systems. They are now faster than ever a...
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  Headline: 📮 New 2026 USPS "Mailbox Rule": Is Your Tax Return Actually Late? Attention! For decades, we’ve relied on the "timely mailed, timely filed" rule. If you dropped your tax return in a blue mailbox on April 15th, the IRS considered it on time. That has officially changed for the 2026 tax season. As of December 24, 2025, a new USPS regulation (Section 608.11) clarifies that a postmark is no longer applied when you drop off your mail. Instead, it’s applied when your mail is first processed at a regional distribution facility. What this means for you: The Postmark Lag: If you drop your return in a collection box on the deadline, it might not reach a processing center until the next day—resulting in a late postmark and potential IRS penalties. The "Rural" Risk: If you are mailing from outside a major hub (like areas around Austin), the lag can be 48 hours or more. 3 Ways to Protect Your Filing: Manual Postmarking: Take your envelope to the count...

Why an Offer-in-Compromise is More of an Art Form Than a Fill in the Blank Form

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  Fairly soon taxpayers will begin receiving IRS collection notices after several years of hiatus during the COVID outbreak. For more information of this development check out this link.      This will trigger the flood of national Offer-in-Compromise mills to put out their “settle your tax debt for pennies on the dollar” and “The IRS writes off millions of tax debt each year”. Both true statements but read the fine print. You must qualify. Ahh, and therein lies the rub. How do I qualify and keep my country club membership, my Tesla lease and shopping at Whole Foods? The short answer is you can’t. Pro Tip - For more information on What is an Offer in Compromise, check out my web page on this subject.   But what about those taxpayers in the middle – who have legitimate, OIC worthy tax situations? How do they communicate that to the OIC processor? Enter the tax artist.   Form 433A is a complete, in your face, disclosure of your entire financial ...

Bulletin - IRS Provides Penalty Relief on 5 Million Returns

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  The IRS announced this week that it was providing about $1 billion in penalty relief to taxpayers who should have received collection notices during the pandemic - specifically applying to 2020 and 2021 tax returns.  The Press Release   has several nuggets beyond the headline penalty relief. These nuggets provide guidance on several topics. Among the interesting items: Quoting from the Press Release - Given this unusual situation, the IRS is taking several steps in advance of resuming normal collection notices for tax years 2020 and 2021 to help taxpayers with unpaid tax bills, including some people who have not received a notice from the IRS in more than a year. (Italics added). This penalty relief is automatic. Eligible taxpayers don't need to take any action to get it. Eligible taxpayers who already paid their full balance will benefit from the relief, too; if a taxpayer already paid failure-to-pay penalties related to their 2020 and 2021 tax years, the IRS wil...

Health Savings Accounts (HSAs) and Flexible Spending Accounts (FSAs)

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  Individuals increasingly turn to specialized accounts like Health Savings Accounts (HSAs) and Flexible Spending Accounts (FSAs) to navigate the complex tax landscape, considering healthcare costs as a significant aspect of financial planning. These accounts offer unique tax advantages and considerations that can significantly impact on your overall financial well-being. Using one of these plans may allow you to lower your tax bill and allows you to maximize the use of your health care dollars – both important considerations in and out of the tax arena. In this article, we will explore the ins and outs of HSAs and FSAs, helping you make informed decisions about your health-related financial planning.   CAVEAT – While this is tax centered discussion, I subscribe to the complex theory of “don’t let the tax tail wag the dog.” By this I mean that while tax considerations are present in most business and personal financial decisions, there may be considerations beyond tax in y...

Navigating the Maze: A Guide to Tax Preparation and Filing

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  Tax season is upon us once again, and for many, it can be a daunting and confusing time. Between gathering documents, understanding deductions, and ensuring accuracy, the process can feel overwhelming. But fear not! This guide will help you navigate the maze of tax preparation and filing with confidence.   Step 1 - Gathering Your Documents:   The first step to successful tax preparation is gathering all necessary documents. This includes:   W-2 forms: These forms report your wages and salaries earned from employers. 1099 forms: These forms report income received from non-employee sources, such as self-employment, freelance work, or investments. 1098 forms: These forms report mortgage interest paid. 1095 forms:   These forms report health insurance information. Receipts and documentation: Keep track of any receipts or documentation for deductions and credits, such as charitable donations, medical expenses, or business expenses. Bank Statem...

Navigating a Complex Landscape: Top Income Tax Issues in the US Today

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  Tax season is right around the corner, but the complexities and controversies surrounding the US income tax system remain a constant source of discussion. From concerns about fairness and inequality to the challenges of navigating a labyrinthine code, the issues at hand are multifaceted and warrant careful consideration. Tax issues are complex and multifaceted. Ask your AI engine of choice and this is the response you’ll receive to the question – “What are the top income tax issues in the US today?”.   Here are some of the more popular responses: The Fairness Debate : One of the most prominent issues revolves around the perceived unfairness of the current system. Critics argue that the tax code favors the wealthy, with lower effective rates for high-income earners due to loopholes and deductions. This disparity raises concerns about the system's ability to ensure equitable contributions from all citizens. Specifically, the treatment of capital gains and dividends h...