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New tax reduction strategies carefully explained and exhaustively researched every two weeks. Receive breaking news updates on tax law changes. Members only monthly AMA with TOTTB.tax.

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2025 Spring Fling Webinar Event

As we prepared our 4th Annual Summer Education Series, our friends at Sandy Bay challenged us to go bigger and do even more live events than we originally planned. So, we did! We are proud to present Think Outside the Tax Box's first ever “Spring Fling” live webinar event. As a monthly or annual subscriber, this webinar is 100% exclusive, and free to you! Every webinar comes with free continuing education credits for those who qualify! Keep reading for more details...

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CURRENT EDITION

2026 Changes to Form 2441 and Dependent Care Benefits

The credit for dependent-care expenses (such as daycare costs) has long been stuck at 20% for “average” taxpayers. It finally gets a permanent boost in 2026 (for returns filed in 2027). Also, the amount of money a taxpayer can put into a dependent care assistance program is increasing by $2,500 for 2026. This change presents a chance for taxpayers and tax pros to reevaluate which is better – claiming the credit or using a flex plan.

Turning Intellectual Property into Interest Deduction Capacity: Use of an IP Holdco After the OBBBA

Many taxpayers have lived with a frustrating mismatch since the Section 163(j) limitation tightened after 2021 – the business may generate plenty of cash, yet its interest deductions are limited because adjusted taxable income (“ATI”) is too low, e.g., due to capex. The 2025 restoration of depreciation and amortization addbacks makes ATI planning relevant again, especially for groups that own valuable intangible property (“IP”), and the choice of legal entity to house group IP may have very different tax consequences as discussed in this article.

Do You Know U.S. Tax History?

In recognition of the 250th anniversary of the adoption of the Declaration of Independence on July 4, 1776, let’s review 250 years of tax history. Our nation’s tax systems have evolved over two and a half centuries as ways of doing business and living have changed. Also, expectations of services the public wants and needs from the government have grown, resulting in tax changes to generate increasing amounts of tax revenue. Along the way, lawmakers have considered principles of simplification, equity, fairness, economic growth and effective tax administration that have shaped our tax laws. This article offers questions and answers to cover a range of interesting aspects of our federal tax history.

SIMPLIFIED TAX STRATEGIES &
PRACTICAL IMPLEMENTATION

Think Outside the Tax Box provides tax reduction strategies along with practical
implementation advice in order to reduce your clients’ federal tax bill with ease.

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