Taxes and Flow-Through Entities in Divorce

When a marriage involving owners of a flow-through entity is on the rocks, the intertwining of personal and business finances can create significant tax complications. This is especially true when one spouse is more involved in the business operations than the other. There are more than just tax issues to consider in divorce. But taxes…

A Government Step Transaction Doctrine

When taxpayers weave together various tax rules to produce a favorable outcome, the IRS will often cite various judicial doctrines to avoid the result or to unwind the transaction. This can include economic substance, the step transaction doctrine, etc. These doctrines allow the IRS to effectively reverse the tax treatment of transactions when multiple tax…

CDP Hearings and OICs: When Does the 24-Month Clock Stop?

When it comes to tax deadlines, taxpayers are often held to strict standards. Miss a filing deadline by a day, and the taxpayer could lose their rights and/or ultimately be stuck with a higher tax balance. But what happens when it’s the IRS that has a deadline to meet? The short answer is that the…

From Commingled to Contested: The IRS’s Audit of Tax Deductions

The common idea that business expenses are deductible while personal expenses are not is an oversimplification. In reality, the tax rules are more nuanced. Some personal expenses are deductible, and the line between personal and business expenses is often blurry. This complexity is further compounded by the fact that many businesses, particularly small ones, fail…

IRS Collections: Different Rules for Foreign Debts?

The United States is built on fundamental principles of rule of law, due process, and justice. These concepts are not merely abstract ideals but are deeply ingrained in our legal system and societal expectations. They form the bedrock of what many consider to be American exceptionalism – a system where laws are transparent, consistently applied,…

Dealing With IRS Audit of a Hobby Loss Activity

The IRS is a silent partner in every business venture. It is quick to take its share of profits when a business venture succeeds. The IRS is often not a good business partner. It often refuses to share in the losses during the down times. This unequal treatment often comes up when the taxpayer reports…

The “Wait & See” Approach to IRS Tax Debts

While owing money to the IRS is not ideal, it is often manageable. One just needs a view of the longer time horizon. As it turns out, in many cases, the IRS never even bothers to attempt to collect unpaid taxes and/or it ends up only collecting a small amount. While there are a lot…

The Rules of the Game: Burden of Proof in Tax Disputes

Every relationship has rules, whether informal or formal. Every human interaction has them too. One can easily see this in forced relationships. Take organized sports, for example. Organized sports are essentially pre-planned interactions governed by specific rules that all parties agree to follow. The effectiveness of the rules hinges on proper enforcement, which often requires…

The Balancing Act: Records Needed for Tax Positions

The Goldilocks Principle says that the best outcomes are achieved by finding a balance. It looks for the “just right”—neither too much nor too little. This concept applies not only to storytelling but also to tax recordkeeping. Taxpayers have to strike a balance in maintaining records that are thorough enough to satisfy the IRS but…

When the IRS Fails to Timely Respond: Who Pays?

The IRS, like many organizations, faced significant challenges during the COVID-19 pandemic. It had to adapt to new working conditions, which led to delays in processing paperwork, including tax returns, and difficulties in responding to taxpayer inquiries. During this time, when a taxpayer could reach someone at the IRS, they were often told that due…