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Think Outside the Tax Box
@tottbnews.bsky.social
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The premier tax reduction source offering biweekly tax saving insights for businesses, individuals, and tax professionals
#taxtwitter #skytax

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The Health Savings Account (HSA) is a first line of defense tax strategy. Contributions are deductible and earnings are tax-free if used for qualified medical expenses.

Make sure to check out Keith Schroeder's article on tackling taxes on an inherited HSA!
#taxes #hsa
https://bit.ly/4rJyJSE
Tackling Taxes On an Inherited HSA - Think Outside the Tax Box
The Health Savings Account (HSA) is a first line of defense tax strategy. Contributions are deductible and earnings are tax-free if used for qualified medical expenses. There are numerous features to ...
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February 13, 2026 at 8:16 PM
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The most recent Tax Court decision on a syndicated conservation easement, Jackson Stone South LLC, highlights the continued difficulties taxpayers encounter in these matters. Peter Reilly reviews the ruling and explores its implications for tax practitioners.
https://bit.ly/4bO2GfR
#taxes #taxcourt
Reflecting On The Conservation Easement Mess - Think Outside the Tax Box
As I write this, the most recent Tax Court opinion on a syndicated conservation easement deal is Jackson Stone South LLC. Good chance there will be another before I finish. Estimates indicate that there are over a thousand docketed cases. Jackson Stone ...
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February 11, 2026 at 7:54 PM
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Check out Peter Reilly's article on tax topics for 2025, that he opened a file on but never managed to make an article with.
#taxes #tax #taxprofessional

https://thinkoutsidethetaxbox.com/articles/tax-tales-i-let-slip-in-2025-from-whistleblowers-to-easement-woes-and-beyond/
Tax Tales I Let Slip in 2025: From Whistleblowers to Easement Woes and Beyond - Think Outside the Tax Box
One of my greatest frustrations as a tax writer is that I just don't have the time to cover everything that I notice. Early in my blogging career, when I was younger and had more energy, I set myself on a Monday, Wednesday, Friday schedule like the coll...
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February 5, 2026 at 4:53 PM
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Bad chemistry with one client can disrupt the flow with everyone. That one client who doesn’t follow your processes and messes up the workflow during tax season. As the firm owner we should do whatever we can to protect good chemistry within our business.
#tax #taxprofessional
https://bit.ly/3Zy8937
Not Every Client Is a Keeper: When Saying Goodbye Protects Your Practice - Think Outside the Tax Box
Bad chemistry with one client can disrupt the flow with everyone. That one client who doesn't follow your processes and messes up the workflow during tax season. The client who never turns things in on time but then wants results from you immediately wh...
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February 3, 2026 at 6:14 PM
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As tax professionals, our effectiveness depends less on how the Internal Revenue Manual says the IRS should operate and more on understanding how it actually operates today.
#taxes #taxnews #tax
Don't miss Joshua Youngblood's article:
https://bit.ly/46miF0R
The IRS in 2025: A Snapshot of Reality - Think Outside the Tax Box
The IRS is not the same agency we dealt with a decade ago, or even three years ago. The pandemic accelerated operational strain, exposing long-standing infrastructure weaknesses while also prompting overdue investment and modernization. Some areas have ...
thinkoutsidethetaxbox.com
January 30, 2026 at 4:53 PM
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Your website’s job is not to impress people with fancy design elements; it’s to speak directly to the problems your ideal clients are trying to solve.

Check out Marie Torossian's article:
#skytax #taxes #tax
https://thinkoutsidethetaxbox.com/articles/your-website-isnt-broken-your-messaging-is/
Your Website Isn’t Broken—Your Messaging Is - Think Outside the Tax Box
I recently attended a two-day marketing workshop that made me think about whether I am effectively communicating with prospects on my websites. I do an annual review of my websites and update them to ...
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January 29, 2026 at 10:15 PM
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Every tax season, well-intentioned taxpayers get lured by false tax advice on social media, only to end up in trouble. As tax professionals, you will encounter clients who need you to untangle the mess.

Check out @joshyoungblood.bsky.social's article!
https://bit.ly/4sOlphj
#tiktok #taxhacks #tax
When TikTok Tax Hacks Backfire: Helping Clients Misled by Social Media Scams - Think Outside the Tax Box
Jessica, a self-employed consultant, was thrilled when she found a viral TikTok video promising a “little-known” tax trick. The video claimed she could get a huge refund by claiming a special Fuel Tax Credit and even writing off her family's beach vacat...
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January 21, 2026 at 6:13 PM
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Don't forget to check out this month's Tax Court Roundup and stay up to date on the latest tax updates!

https://thinkoutsidethetaxbox.com/articles/tax-court-roundup-january-2026/
#taxes #taxnews #tax
TAX COURT ROUNDUP - January 2026 - Think Outside the Tax Box
Though 2025 was a gamechanger in many ways, Tax Court went on resolving controversies both arcane and mundane. Inventive counsel tried extending Supreme Court pronouncements and stretching narrow juri...
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January 20, 2026 at 8:07 PM
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When most people think about saving for the future, their minds jump to retirement accounts—401(k)s, IRAs, maybe even defined benefit plans. But business owners have another option that often goes overlooked: using a C corporation as a strategic savings vehicle.

https://bit.ly/45TkdiG
#taxes #tax
January 15, 2026 at 5:07 PM
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You’ve got a packed calendar, a nonstop inbox, and maybe even a waitlist. But if your client list feels more like a burden than a blessing, you’re not alone. What if the secret to a more profitable and fulfilling practice wasn’t more clients—but better ones?

https://bit.ly/3NkStgy
#taxes #tax
How to Build a Better Client List (and Why It Matters More Than You Think) - Think Outside the Tax Box
You've got a packed calendar, a nonstop inbox, and maybe even a waitlist. But if your client list feels more like a burden than a blessing, you're not alone. Many tax professionals find themselves weighed down by clients who are difficult, unprofitable,...
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January 13, 2026 at 7:47 PM
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Special Offer - Get $50 OFF a 1 Year Subscription!

Tap into the latest tax planning ideas, practice management tips, and industry updates delivered to your inbox twice a month.

Think Outside the Tax Box is the Ultimate Newsletter for Tax Professionals Now you can save $50 on a 1 Year Subscription!
January 8, 2026 at 4:49 PM
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In mid-November, a portrait of a young Vietnamese woman by Gustav Klimt, from the estate of the late Leonard Lauder, sold at Sotheby’s for $236.4 million. According to Bloomberg, it now holds the record as the most expensive modern artwork ever sold at auction.
https://bit.ly/4jxZN4H
#taxes #tax
Fractional Art Investing Is Real -- How To Advise Your Clients On The Tax Consequences - Think Outside the Tax Box
In mid-November a portrait of a young Vietnamese woman by the artist Gustav Klimt, which was part of the estate of the late Leonard Lauder (the cosmetics billionaire), was sold at a Sotheby's auction for $236.4 million. It set the record for the most ex...
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January 7, 2026 at 6:55 PM
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So as I did last year, I have reviewed a multitude of year-end tax tips articles. I will give you a few suggestions that stand out as different that I will get into a little more along with some thoughts of my own.

Check out Peter Reilly's Year-End Tax Tip Guide: https://bit.ly/4qtZABA
#taxes
January 5, 2026 at 9:52 PM
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Check out Marie Torossian's article where she discusses how you can leverage the power of AI bots to efficiently handle FAQs and convert prospects into clients, all while saving precious time and resources.

https://bit.ly/4aBw08F
#taxplanning #ai #taxes
Effortlessly Convert Leads: How AI Bots Can Handle FAQs and Drive Appointments for Accountants - Think Outside the Tax Box
AI technology, particularly in customer service automation, is now more accessible than ever. AI-powered bots are a powerful tool for businesses, including accounting firms, empowering them to improve...
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January 3, 2026 at 4:10 PM
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Is the taxidermy fee for a stuffed bear deductible? If so, should I depreciate it? What would the basis and class life be for depreciation? Those are real questions asked in a group chat with some colleagues.

Check out Amber Gray-Fenner's article now: https://bit.ly/4aGiOzt
#taxes #taxplanning
Taxes & Taxidermy: Rampaging Through The Tax Code On The Back Of A Stuffed Rhinoceros - Think Outside the Tax Box
Is the taxidermy fee for a stuffed bear deductible? If so, should I depreciate it? What would the basis and class life be for depreciation? Those are real questions asked in a group chat with some colleagues. Of course my answer was “It depends.” And, l...
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January 2, 2026 at 9:12 PM
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In this end of year round-up, Dominique Molina curates the most strategic, high-impact moves to make before the end of the year so you can start out 2026 on top.
https://bit.ly/3XTJBAL
#taxsky #taxes #OBBBA
Year-End Tax Planning Under the One Big Beautiful Bill Act (OBBBA) - Think Outside the Tax Box
The One Big Beautiful Bill Act (OBBBA), signed into law on July 4, 2025, doesn't reinvent the tax code it refines it. Much like its predecessor, the Tax Cuts and Jobs Act (TCJA), it keeps many familiar provisions in play: lower rates, expanded SALT flex...
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December 18, 2025 at 5:13 PM
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Join Jennifer Baker and our friends at Foxstone for the last webinar of the winter series tomorrow at 11am PST!
https://thinkoutsidethetaxbox.com/articles/2025-winter-education-series-event-calendar/
#taxes #taxsky #skytax
December 15, 2025 at 11:40 PM
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With permanent bonus depreciation now in place, many investors are returning to the classic approach of leveraging rental property purchases and accelerating deductions. Roger Ledbetter breaks it down in his article:
https://bit.ly/4pzBqWv
#taxes #taxpros #tax
Timing is Everything: A Conversation Between a Tax Pro and Client - Think Outside the Tax Box
The new permanent bonus depreciation regime will bring back the old playbook: lever up to buy a rental property and bonus depreciate everything under the sun. But the tax savvy general partners know that WHEN to depreciate is just as important as how to...
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December 12, 2025 at 5:11 PM
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In Part 2 of our OBBBA student loan series, Caitlin See explores how these changes could play out for common borrower situations and what advisors should be aware of to confidently guide clients through the post-OBBBA student loan landscape.
https://bit.ly/4rJ8mx9
#tax #taxes #taxnews #OBBBA
Student Loans After the OBBBA Part 2: Helping Clients Navigate the New Landscape - Think Outside the Tax Box
As the federal student loan system enters a new era, advisors are tasked with helping clients navigate the practical implications of recent reforms. The One Big Beautiful Bill Act (OBBBA) has redefined borrowing limits and repayment options, creating fr...
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December 9, 2025 at 6:07 PM
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Part of getting the most from your return is about understanding the definitions of the IRS. Two that seem very similar but have distinctly different consequences on your taxes, are real estate dealer and real estate investor.

Check out Kim Larsen's article now:
https://bit.ly/3MfGNv2
#taxes #tax
Are You a “Real Estate Dealer” or “Real Estate Investor” for Tax Purposes? - Think Outside the Tax Box
Tax law is forever classifying people and making structures that either create benefits or disadvantages on your tax return. Part of getting the most from your return is about understanding the definitions of the IRS. Two that seem very similar but have...
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December 5, 2025 at 5:11 PM
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Most tax pros will miss the biggest opportunities in the new Big Beautiful Tax Bill. You won’t — if you know where to look. Discover how to turn OBBBA into your next tax planning advantage with insights from Think Outside the Tax Box.

https://bit.ly/4rCqtEV
December 4, 2025 at 8:08 PM
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Join us TOMORROW December 4th at 11am PST for Building Blocks for Long Term Tax Efficiency with Todd Lofgren from our sponsors Alternative Tax Management!
https://thinkoutsidethetaxbox.com/articles/2025-winter-education-series-event-calendar/
#taxes #skytax #taxpros
December 3, 2025 at 5:50 PM
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Happy Thanksgiving to our Think Outside the Tax Box community! We hope you enjoy time with loved ones and plenty of yummy food. We're truly grateful for each of you, thank you for your support and for being such an important part of our journey😊🦃
November 27, 2025 at 4:49 PM
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The Big Beautiful Tax Bill isn’t just legislation. It’s a roadmap to untapped savings and smarter strategy.

Download your FREE Copy of "How to Turn the OBBBA Into Real Client Savings" Today!
https://bit.ly/4oYOOTw
#taxes #OBBBA
November 25, 2025 at 5:13 PM
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The One Big Beautiful Bill Act, signed into law by President Trump on July 4, 2025, added a new tax saving tool for minors, the aptly named Trump Accounts.

In this article, Tyler Menzer CPA, PhD goes over the details of the new Trump Accounts: thinkoutsidethetaxbox.com/articles/an-...
#taxes #tax
An Analysis of the OBBBA's Trump Accounts (Part 1) - Think Outside the Tax Box
The One Big Beautiful Bill Act, signed into law by President Trump on July 4, 2025, added a new tax saving tool for minors, the aptly named Trump Accounts. In this article, I go over the details of th...
thinkoutsidethetaxbox.com
November 14, 2025 at 7:58 PM