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The 1099 Nightmare

My attitude toward 1099 compliance changed radically about fifteen years ago. The type of 1099 compliance I am talking about is for business to business services. If you are running a bank or a brokerage house, this will not be any help. I was a partner in a regional firm and frankly I never gave 1099 compliance much thought until I was called in to consult on an audit. Then I got this really scary wake-up call...

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CURRENT EDITION

What Happens If You Can’t Use All Your Clean Energy Tax Credits This Year?

Clean energy tax credits have a lot going for them. Clients buy them at a discount, apply them dollar-for-dollar against federal tax liability, and walk away paying less to the IRS. That alone makes them worth a serious look. But here’s what often gets overlooked and what makes these investments genuinely remarkable compared to almost anything else in your tax planning toolkit: the flexibility built into how and when the credits can be used. Can’t absorb the full credit this year? Carry it back up to three years and trigger refunds on taxes your client already paid. Think about that for a second. There are very few places in the tax code where you can go back in time and rewrite last year’s tax bill. This is one of them. Still have excess after the carryback? Carry it forward for up to 22 years. That’s not a typo. Two decades of runway to put those credits to work as your client’s passive income grows. And if circumstances change and the credits simply aren’t needed? An emerging secondary market means there may even be an option to sell them. No other common tax planning strategy offers this combination a guaranteed discount on purchase, dollar-for-dollar offset of tax liability, the ability to look backward and forward, and a potential exit if plans change. Understanding how each of these features works is what separates a good credit investment from a great one.

Perspectives on IRS Scrutiny of Captive Insurance Elections

The Internal Revenue Service has made no secret of its increased scrutiny of captive insurance arrangements, particularly those involving the small insurance company election. For taxpayers and their advisors, this has created understandable concern and, in some cases, hesitation about whether captive insurance remains a viable risk management and tax planning tool. Yet heightened scrutiny does not mean prohibition. The Internal Revenue Code continues to recognize captive insurance, Congress has refined it, and courts evaluate it based on well-established insurance principles. The real issue is not whether captives are allowed, but whether a specific taxpayer has a legitimate business need for insurance, has structured the arrangement properly, and has implemented it in a manner consistent with both tax law and insurance fundamentals. Understanding where scrutiny arises, how elections function, and what separates compliant captives from problematic ones is critical for CPAs advising closely held businesses today.

Explore Our Free Articles

Get a taste of our comprehensive tax planning insights with four featured articles, free for everyone.

2026 Summer Education Series Event Calendar

Think Outside the Tax Box is thrilled to bring you the 2026 Summer Education Series, sponsored by Sandy Bay! The fifth installment of this beloved annual series, we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax all summer long. Each webinar will

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Contracts, Signing Bonuses, and the Substantial Presence Test

In tighter job markets, recruits are often offered signing bonuses (and sometimes moving expenses) to join a firm. Sometimes construction workers temporarily relocate to jobs in other states while they are employed by the company that hired them in their home state. This article reviews some of the foundational tax

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As an annual subscriber, you gain complimentary access to our series of expert-led webinars. Each session is designed to provide you with insights, skills, and knowledge to excel in your field. Discover what’s coming up and secure your spot today.

Inventory Expensing and The Cash Method: Changes from the TCJA

Join Lucien P. Gauthier as we discuss these two changes made by the TCJA in depth.​

Taking the Mystery Out of Revised Energy Credits for Individuals

Learn valuable tips to help your clients claim the new residential energy and electric vehicle credits.

Tax Season 911

Your preparedness plan to create tax savings and survive the busiest of times without falling into old habits!

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Featured Authors

Amber Gray-Fenner is an Enrolled Agent and tax practitioner specializing in tax returns, planning, and representation for individuals and small businesses. She owns Tax Therapy, LLC in Albuquerque, New Mexico.

Matt Metras, EA, owns MDM Financial Services in NY, specializing in bookkeeping and taxation for cryptocurrency clients. He’s an educator on cryptocurrency taxation and actively engages in community advocacy.

Jeff Stimpson, has been a tax and finance writer for 25 years. Hee contributes to publications like Accounting Today and Financial Advisor. His other credits include sales tax, technology, and practice management, residing in New York.

Annette Nellen is a professor and tax program director at San José State University, with extensive involvement in tax organizations and a focus on tax policy, cryptocurrency, and education.

Peter J Reilly graduated from the College of the Holy Cross, worked in CPA firms like Joseph B Cohan and Associates and CCR LLP, and now runs a tax practice while writing for Forbes.com.

Thomas Gorczynski, EA USTCP CTP, is a tax expert known for speaking and educating on federal tax law. He’s editor-in-chief of EA Journal, co-author of the PassKey Learning Systems EA Review Series, and runs a tax practice in Phoenix, Arizona.

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Quotes from users who have benefited from Tax Law Pro, highlighting how it has helped them in their tax planning and compliance efforts.

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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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