CURRENT EDITION

Breaking Down Tax Benefits for Higher Education
With the rising cost of higher education and greater reliance on student loans, taxpayers are looking for every opportunity to ease the financial burden of earning a degree. Fortunately, several higher education tax benefits are available to help offset the high cost of tuition, student loans and other education-related expenses. However, certain eligibility requirements — such as income limits and tax filing status — often trip up taxpayers along the way. Understanding the nuances of these tax benefits for higher education can ensure your clients take full advantage of available tax savings.
READ MOREWay Out of State Tax on Student Debt Forgiveness
There was some rain on the parade of celebration of the student loan debt forgiveness. The Tax Foundation, perhaps with a touch of schadenfreude, announced that the forgiveness, not federally taxable due to recent legislation, might be taxable in as many as thirteen states. They have taken a closer look and backpedaled quite a bit. It is now down to four states Minnesota, Mississippi, North Carolina and Wisconsin and those are not for sure. But, there is likely another way out for many of the recipients of this boon. Keep reading to learn more!
Read MoreFully Funding Your HSA
It's 4th quarter, soon taxpayers will be reaching out to their trusted advisors. They will want to see what they can do last minute to save on taxes. There isn't much you can do at the end of the year. Still, these taxpayers will reach out expecting you to wave a magic wand and save them a few thousand dollars. Well, this year you may be able to do just that. Even if they have already maxed out their retirement accounts. Taxpayers are not restricted from using this strategy by income or self-employment. Are you ready to add this triple tax advantaged savings tool to your bag of resources?
Read MoreLive Event! Reasonable Compensation for S Corps Webinar
A TOTTB Live Webinar Event sponsored by our friends at RCReports! For two decades the IRS has been preparing an assault on reasonable compensation for S Corps. Their arsenal is now fully locked and loaded. In it, there is everything from commonsense tools to obscure memos. We will explore key court cases, IRS guidelines, preparer penalties and some of the obscure weapons the IRS has put in place. We debunk common myths and fiction on how reasonable compensation should be calculated and replace it with facts and methodologies that the IRS relies on.
Read MoreTax Disaster Relief – More Than Just Return Extensions
Evie and I withdrew from active tax practice in 2018, but she maintains a sort of family and friend's freebie practice using Drake. I help a little. We have been struggling with difficulty getting the information for one of our “clients” as we watch the ultimate October 15 deadline creeps up on us. She is in Florida in one of the counties covered by President Biden’s disaster declaration relative to Hurricane Ian. So it was sort of a relief to find out that we have another three months to get the return done. In this case it is not a huge benefit since interest will still clock if there turns out to be a balance due, since the payment was due on April 18. “Certain deadlines” falling on or after September 23, 2022 and before February 15, 2023 are postponed through February 15, 2023. Read on to learn more!
Read MoreIs a Self-Directed Crypto IRA a Good Idea?
Self-directed IRAs (SDIRAs) have long been a vehicle for less traditional investments that can't be held in a normal IRA, such as precious metals, real estate, or tax liens. Cryptocurrency is the newest addition to that list of alternative retirement savings and has exponentially grown in popularity in recent years. The rules governing SDIRAs are complex, and taxpayers can easily and unknowingly violate the rules, resulting in the entire IRA being deemed distributed and potentially subject to tax. As the famous adage says, "with great [investment] power comes great responsibility." Keep reading to learn more!
Read MoreJust Good Business – Review and Shop Your Financial Accounts
The fourth quarter just started and it's time to have your clients take a look at their financial services game plan. With interest rates approaching historic highs now is the time to review financial accounts to ensure high returns on cash investments, optimize reward-bearing accounts, and minimize interest paid and fees for financial products and accounts. The goal of this review is to ensure that investments and rewards programs are tuned for optimal results and to minimize interest and fees throughout next year. I won’t be providing much in the way of specific, prescriptive advice. I am not a registered investment advisor or a certified financial planner, nor do I recommend specific products, services, or institutions (other than a subscription to this publication). Rather, I will be providing a framework for the review, encouraging you to ask good questions about the goals for the various accounts, and reminding you to consider the big picture as well as the role each part plays in it. Let’s get started!
Read MoreHow to Avoid Losing Valuable Noncash Charitable Contributions
The rules for noncash charitable contributions defy easy summary. On the other hand, they are not rocket surgery. Moving on from the humor, if you want to sum them up in a sentence you can use Reilly’s Seventh Law of Tax Planning: Read the instructions. Specifically, you want to read the instructions to Form 8283 Noncash Charitable Contributions. There is, of course, more to it than that, but you will find a remarkable number of disallowed deductions from not following those instructions. To be fair, sometimes there are other shenanigans going on and the instruction failures are the easiest way for the IRS to attack. Nonetheless, there is nothing to say that the IRS will not use the precedents set in those cases on your client even though they are not trying to get away with anything. To get a simplified list of what to know and implement, continue reading.
Read MoreShould Your Practice Use a Client Portal?
You may know me as the “crypto guy” here at Think Outside the Tax Box. It might seem like that’s all I ever write about. But this time, I’m sneaking an article in while my editor is on vacation. Because I want to talk about using a client portal and why all tax professionals should be using one in their firms. Some firms may have dipped their toe into the digital waters out of necessity as a by-product of the pandemic. Others may have started the process long before Covid existed. According to a completely unscientific poll I ran on Twitter, 70 percent of firms are still processing returns at least partially on paper. This can mean either receiving paper documents from a client or delivering a hard copy of the completed return to the client. As the numbers from a Twitter survey are clearly biased toward firms already comfortable with digital technology, we can safely assume more accurate numbers are significantly higher. Since TOTTB refuses to provide me with a budget to run a full, comprehensive study, we’ll just have to run with my perfunctory data as well as published data from a poll Canopy conducted in 2021. Canopy surveyed more than a thousand small businesses and found that 63 percent admitted that their accountant did not offer any portal. More surprising, depending on whom you ask, is that more than two-thirds of respondents said they would be interested in switching to an accountant that allows them to use photos of their documents for easy sharing. While I’m not here to debate the issues of opening a gajillion .jpg files and how that might negatively affect my practice, the impact of using technology can improve your efficiencies, communications, and improve your workflow. To learn how, continue reading.
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CURRENT EDITION

Breaking Down Tax Benefits for Higher Education
With the rising cost of higher education and greater reliance on student loans, taxpayers are looking for every opportunity to ease the financial burden of earning a degree. Fortunately, several higher education tax benefits are available to help offset the high cost of tuition, student loans and other education-related expenses. However, certain eligibility requirements — such as income limits and tax filing status — often trip up taxpayers along the way. Understanding the nuances of these tax benefits for higher education can ensure your clients take full advantage of available tax savings.

Don’t Forget About the Refund Statute Expiration Date
Have you ever found an amazing strategy for a new tax prospect that they missed in previous years? Even worse, have you realized that you overlooked a client’s eligibility for a credit when you prepared their tax return? Not only that, but you had them make an unnecessary estimated tax payment. Well, it may not be too late for your client and prospect to take advantage of those credits for the year in question. The fate of your client isn’t sealed after filing their tax return. The IRS gives taxpayers a set amount of time to make a claim for a credit on their return. The IRS calls the date that this time sunsets the Refund Statute Expiration Date.

Syndicated Conservation Easement Promoters Continue to Lose In Tax Court
The Tax Court docket has been inundated with syndicated easement cases. In 2024, the IRS was mostly winning. That trend has continued in 2025. So far there have been three IRS wins. Here they are.