How to Substantiate Gambling Tax Losses

There are several types of tax disputes that are frequently litigated. Gambling losses are an example. Taxpayers who gamble often incur significant losses. If the taxpayer is found to be a professional gambler, these losses can be counted for income tax purposes and used to offset the taxpayer’s other income. These tax losses can reduce…Continue readingHow to Substantiate Gambling Tax Losses

Correcting Tax Overpayments After the Refund Period

There are times when tax deadlines are strict. They cannot be changed. The time period for filing a refund claim is an example. Taxpayers generally have the later of three years from the filing of a return or two years from the payment of the tax to file a refund claim. But what if the…Continue readingCorrecting Tax Overpayments After the Refund Period

IRS Expands Sec. 9100 Relief for Late Forms 3115

As innocuous as it sounds, the Form 3115 is a tax form like no other. A Form 3115 that is inadvertently omitted from a tax return filing can result in sizable differences in tax and trigger significant tax penalties and interest. Given the amounts that are often reported on the Form 3115, errors could cost…Continue readingIRS Expands Sec. 9100 Relief for Late Forms 3115

Converting Home to Rental to Get Tax Loss Deduction

If you move out of a house and rent it to a friend for less than fair market value rent, can you then take a tax loss on the subsequent sale of the house? If the home is not converted to a rental property, the loss is disallowed as a personal tax loss. If the…Continue readingConverting Home to Rental to Get Tax Loss Deduction

Tax Court Puffery: Exaggeration is Not Evidence

Every communication makes statements. The statements may be truthful or false. A statement that is misleading or exaggerated is somewhere between these two. There can be significant legal consequences depending on where a statement falls on this continuum. This raises questions as to how precise do the statements have to be to be false? If…Continue readingTax Court Puffery: Exaggeration is Not Evidence

Funeral Expense Organization Denied Nonprofit Status

Gargamel, the antagonist in the Smurfs, is the villain. Wile E. Coyote in the Road Runner, Raquelle in Barbie, Lex Luther in Superman, the Joker in Batman, Darth Vader in Star Wars. The list goes on. That is one side of these stories. It’s the side of the story that is presented to us. It…Continue readingFuneral Expense Organization Denied Nonprofit Status

Rejected e-File Return is a Valid Tax Return

The IRS’s Identity Protection Personal Identification Number (“IP PIN”) is intended to protect those who are victims of identity theft. It does so by making it harder for third parties to file fraudulent tax returns. The IP PIN can also cause problems for taxpayers. This is particularly true for tax returns that are filed close…Continue readingRejected e-File Return is a Valid Tax Return

Meal & Entertainment: The IRS Auditors “Bread & Butter”

I once worked with an IRS agent who would only make two types of adjustments. He would make UNICAP/inventory adjustments and meal and entertainment adjustments. If either of these items could be adjusted for a tax return, he would adjust them. It didn’t matter what else was listed on the tax return. It did not…Continue readingMeal & Entertainment: The IRS Auditors “Bread & Butter”

Tax on Virtual Currency Received for Microtasks

Our Federal income tax laws take a broad view of what counts as income and gain. The tax law then imposes a ridged framework for classifying and computing tax on income or gain. By casting the net wide, the tax law is able to capture just about every type of transaction that one could dream…Continue readingTax on Virtual Currency Received for Microtasks

Illness as a Defense to Late Filing Penalties

Will the IRS penalize you if you are unable to file your tax return on time due to the burden of caring for a loved one with COVID? The IRS has not provided penalty relief for taxpayers impacted by COVID-19. The existing penalty relief rules may provide a remedy for some taxpayers. These rules do…Continue readingIllness as a Defense to Late Filing Penalties

What is a Rental Activity?

The ability to generate current year tax losses is a strong incentive for high-income taxpayers to own real estate. Real estate often produces tax losses, but not economic losses. This happens because the current operating expenses plus tax depreciation result in a current year loss. At the same time, the property likely increased in value…Continue readingWhat is a Rental Activity?

Divorce Payments & Tax Basis in Business

Our Federal income tax laws often build upon the presumption that seemingly adverse parties are actually adverse. Our tax laws do not always account for instances where the parties are actively working in concert to reduce the IRS’s cut. Transfers and payments made in relation to divorce are an example. With our tax laws, it…Continue readingDivorce Payments & Tax Basis in Business

Does an IRS Audit Waive a Defect in Tax Return?

When it comes to technicalities in the tax law, the failure to comply with some technicalities can be overcome. Others cannot. As a general rule, the courts evaluate tax disputes involving technicalities based on the policy underlying the technicality versus fairness for requiring strict compliance. If the policy for the technicality is important, the court…Continue readingDoes an IRS Audit Waive a Defect in Tax Return?

When is Rental Real Estate a Business?

Our tax laws are not perfect. There are grey areas. Most of these grey areas are of little consequence as they do not have a significant impact on the amount of tax that is due. There are other grey areas that can significantly impact the amount of tax due. These tax disputes are frequently litigated.…Continue readingWhen is Rental Real Estate a Business?

Avoiding Tax on Discharge of a Mortgage

There are times in life when you may feel that you can’t get ahead. One step forward, two steps back–as they say. Paying income tax on debt that you avoid is an example. You negotiate with the lender or creditor and they agree to settle the balance for less. One step forward. Then a few…Continue readingAvoiding Tax on Discharge of a Mortgage

Avoiding the 60-Day IRA Rollover Requirement

If a taxpayer takes money out of their retirement account, they generally have to pay income tax on the amount distributed. What if the taxpayer wants to put the money back into the account? There have been several examples where Congress has allowed taxpayers to put money back into their accounts. The recent CARES Act…Continue readingAvoiding the 60-Day IRA Rollover Requirement

The IRS’ Power to Fish for Records

Taxpayers often do not want the IRS to have access to their information. This is understandable. The IRS has had problems keeping taxpayer information confidential. Take the case of Ward v. United States, 973 F. Supp. 996 (D. Colo. 1997). In that case, the IRS director and agent disclosed the taxpayer’s information in a live…Continue readingThe IRS’ Power to Fish for Records

Avoid Tax by Returning Pay

There are times when a business structure or transaction no longer makes sense. This may be due to a change in the business environment, such as swings in the economy or unexpected gains or losses. It can also arise due to a change in the owners’ personal circumstances, such as a divorce or death of…Continue readingAvoid Tax by Returning Pay

Worker Reclassification: Degree of Control

The Groundhog Day movie from the 90’s starring Bill Murray portrays a news anchorman who lives the same day over and over again. He is stuck in a loop. Each day starts the same way. Bill tries to alter his conduct and he interacts with different people throughout the movie. The other characters act and…Continue readingWorker Reclassification: Degree of Control

Avoiding Gift Taxes With Formula Clauses

Congress has slowly upped the amount that can be transferred free of estate and gift taxes. This amount has changed over time. It was $1 million in 2003. It is now just over $11.5 million in 2020. This means that many people do not need to worry about estate and gift taxes. Estate and gift…Continue readingAvoiding Gift Taxes With Formula Clauses

Deducting Interest for More than One Home

The mortgage interest deduction seems simple enough. The Code provides a deduction for mortgage interest that is paid during the year. It starts with a broad grant: There shall be allowed as a deduction all interest paid or accrued within the taxable year on indebtedness. Then these 18 words in a single sentence are followed…Continue readingDeducting Interest for More than One Home

Tax Planning for Contingent Loans

Tax is often about timing. Timing issues are those where the taxpayer defers the requirement to pay taxes to a later date. Preferably a later date that is many, many years in the future. The hope is that the taxpayer can retain the amounts that would have been paid in tax today and use the…Continue readingTax Planning for Contingent Loans

Limited Partner Subject to Self-Employment Tax

When it comes to tax law, there are quite a few known-unknowns. These are tax questions that have been raised tangentially in court cases and rulings, but have not been fully answered. These situations confuse taxpayers. Tax practitioners are often asked to provide answers. The answers from tax practitioners often differ, as practitioners have different…Continue readingLimited Partner Subject to Self-Employment Tax

Tax Court Clarifies Employee Tool Plans

Prior to the Tax Cuts and Jobs Act (“TCJA”) of 2018, it was common for employers to simply pay employees more and leave it to the employees to deduct their employee business expenses on their personal income tax returns. The TCJA limited the employee’s ability to deduct employee business expenses. Many employers responded by adopting…Continue readingTax Court Clarifies Employee Tool Plans

Fixing Trust Fund Recovery Penalties

The public may not be fully cognizant of this, but, the IRS is in the business of processing information and making decisions. It accomplishes this by siloing work on tax returns and accounts. The siloed work is intended to allow the IRS to process and make consistent decisions based on a very large volume of…Continue readingFixing Trust Fund Recovery Penalties

Electing Out of the Partnership Audit Regime

When it comes to income taxes and IRS audits, there are a lot of procedural rules that are counter-intuitive. Even if one thinks they are half-baked, the rules are the rules. They can have serious consequences. The centralized partnership audit regime is an example. Tax advisors often instruct their clients to elect out of the…Continue readingElecting Out of the Partnership Audit Regime

IRS Audits for Insolvent Taxpayers

When times are good, we don’t need to worry about the tax loss rules, the net operating loss (“NOL”) rules, or even the bankruptcy tax rules. But these rules are front and center in most tax planning and advice during and after an economic downturn. We saw this with the 2001 dot com bust, the…Continue readingIRS Audits for Insolvent Taxpayers

Taxes & Defunct Texas Corporations

Our Federal tax laws often look to state law. Differences in state law can expand or limit the IRS’s ability to assess and collect Federal taxes. In Patrick’s Payroll Services, Inc. v. Commissioner, T.C. Memo. 2020-47, the court considers whether a defunct Michigan corporation can bring suit against the IRS. This case provides an opportunity…Continue readingTaxes & Defunct Texas Corporations

Texas Franchise Tax: What are COGS?

With advance tax planning, it is often possible to avoid the Texas franchise tax. If the tax does apply, it can often be minimized by a close reading and application of the rules. The recent Sunstate Equipment Co., LLC vs. Comptroller of Public Accounts, No. 17-0444 (Tex. 2020) case provides an opportunity to consider when…Continue readingTexas Franchise Tax: What are COGS?

Whistleblower Claim Limited by Sequestration

We help claimants submit whistleblower claims. But when we receive calls asking for help with whistleblower claims, we do everything we can to dissuade the callers from submitting claims. The IRS’s whistleblower program has been plagued by mismanagement. Cases have long been mishandled by the IRS. Legitimate awards denied. Claimants have to be prepared to…Continue readingWhistleblower Claim Limited by Sequestration

Using Contract Law to Avoid IRS Interest

Interest that accrues on taxes can be abated due to IRS errors or delays. The law that implements this general rule often fails to provide a meaningful remedy in most interest abatement cases. But what about contract law? Can contract law provide another means for obtaining a remedy in interest abatement cases? The court addresses…Continue readingUsing Contract Law to Avoid IRS Interest

IRS Contacts With Government Agencies

The IRS considers information from third parties during audits and in collecting unpaid taxes. The IRS’s efforts to gather this information can significantly harm the taxpayer, as third parties may not want to do business with the taxpayer given the IRS inquiry. Recognizing this, Congress has imposed rules that limit the IRS’s ability to make…Continue readingIRS Contacts With Government Agencies

Property Rights & IRS Levies: Louisiana’s Usufruct

To determine whether the IRS can levy or take property, one has to consider what property the taxpayer owns. State law dictates what property the taxpayer owns. The property laws in most states are similar, which makes applying Federal tax collection law relatively easy. But then there is Louisiana law. Louisiana law differs in many…Continue readingProperty Rights & IRS Levies: Louisiana’s Usufruct

The Tax Preparer’s Right to Appeal Return Penalties

The IRS has been focusing on tax return preparer audits. The aim of these audits is to impose penalties on tax return preparers. The IRS typically provides a means for tax preparers to appeal these penalties administratively, but there are cases where it doesn’t provide this opportunity. In those cases the IRS will assess the…Continue readingThe Tax Preparer’s Right to Appeal Return Penalties

S Corp Election Terminated by Standard LLC Language

If you make an S corporation election and do not fix the standard language that is typically included in the LLC company agreement, you’ll void the S corporation election. This is an issue that is usually identified by during an audit by the IRS. Many taxpayers overlook this issue until it is too late (it…Continue readingS Corp Election Terminated by Standard LLC Language

Can You Rely on IRS Statements?

If you ask someone a direct question and the person responds with incorrect information, is the person bound by their misrepresentation? This raises questions of “estoppel,” which apply to most litigants. But does it apply to IRS employees who make a misrepresentation? Put another way, can you rely on statements by IRS representatives? The court…Continue readingCan You Rely on IRS Statements?

The Late Mark-to-Market Election

Those who trade stocks can take advantage of the mark-to-market election to convert capital losses into ordinary losses. This election is only available to “traders.” There are often questions as to when a taxpayers trading activities are sufficient to warrant being treated as a “trader” for tax purposes. By the time the taxpayer discovers that…Continue readingThe Late Mark-to-Market Election

Substantial Authority, When the Authority is Not Clear

What if you have a tax question and find a court case that: (1) has the same facts as your case, (2) addresses the same tax item as in your case (such as a tax deduction, credit, etc.), and (3) the court case is decided in the taxpayer’s favor, but the court case does not…Continue readingSubstantial Authority, When the Authority is Not Clear

About Tax Preparer Penalty Audits

The IRS’s power to regulate tax return preparers was limited by the Loving v. Internal Revenue Service, 742 F.3d 1013 (D.C. Cir. 2014) line of cases. These cases generally limit the IRS’s ability to regulate tax preparer conduct at an administrative level. But the IRS still has a number of tools at its disposal to…Continue readingAbout Tax Preparer Penalty Audits

Tax Loss Planning: The At-Risk Rules

Are you purchasing a business or real estate that involves financing a business or investment that is likely to produce tax losses in the future? Or have you already made the purchase? If so, there may be ways to ensure that you can take the loss in the future. To do so, you have to…Continue readingTax Loss Planning: The At-Risk Rules

When Clients Testify Against Their Tax Preparer

The IRS has been focusing on examinations of tax return preparers. These examinations often result in the imposition of civil penalties under Section 6694 and 6695. But they can also result in criminal liability for the tax return preparer. The criminal sentencing guidelines can be problematic for tax return preparers. The Keleta v. United States,…Continue readingWhen Clients Testify Against Their Tax Preparer

Fix to Duplicate IRS Address Problem

The IRS sends taxpayers letters and notices from quite a few different IRS offices. As a result, taxpayers are often confused as to what IRS office to respond to. This is particularly true if the IRS letter or notice includes more than one IRS address. The IRS has maintained a harsh stance on taxpayers who…Continue readingFix to Duplicate IRS Address Problem

The Mailbox Rule Extends Time to Recoup Tax Refund

Taxpayers often miss tax filing deadlines. This is even true when the IRS owes the taxpayer money back. Taxpayers have a limited time to request a refund of overpayments. The recent Harrison v. Commissioner, No. 3:19-cv-00194 (2nd Cir. 2020) case provides an opportunity to consider these rules–particularly the mailbox rule. Facts & Procedural History This…Continue readingThe Mailbox Rule Extends Time to Recoup Tax Refund

Can “Business Synergies” be an Asset that Increases a Tax Loss?

The tax consequence of a transaction often depends on how one characterizes or describes the transaction. Business synergies are often cited as the rationale for merger and acquisition deals. In a M&A deal, are “business synergies” a separate asset for tax purposes? Can you list “business synergies” as a separate asset and then take a…Continue readingCan “Business Synergies” be an Asset that Increases a Tax Loss?

Timing for Written IRS Manager Approval for Penalties

The courts recently held that penalties have to be abated if the IRS does not obtain written manager approval for the penalties. The IRS has been abating penalties for this since the ruling. But there is a question as to when does the IRS have to obtain manager approval? Is it sufficient that the IRS…Continue readingTiming for Written IRS Manager Approval for Penalties

An Impartial IRS Office of Appeals

While IRS auditors and IRS attorneys typically focus on imposing the most tax possible, the IRS Office of Appeals does not. Appeals is tasked with settling cases. In doing so, Appeals is supposed to be impartial. This allows Appeals to ‘get it right.’ The recent Onyeani v. Commissioner, T.C. Memo. 2020-15 provides an opportunity to…Continue readingAn Impartial IRS Office of Appeals

Big Tax Savings With ESOP, But Requires Work

An employee stock ownership plan (ESOP) can produce significant income tax savings. This tax savings isn’t exactly free. One has to keep up with the ESOP and the relevant rules to ensure that the tax savings are achieved. This compliance work is required and failure to comply can be costly. The recent Ed Thielking v.…Continue readingBig Tax Savings With ESOP, But Requires Work

Tax Planning for the Start-up Limitation Rules

Our tax laws include start-up rules that limit the ability to deduct certain business and investment expenses. For business owners and investors with other sources of income, this can result in funds being sent to the IRS to pay taxes at a time when the capital is needed to fund the business or investment growth.…Continue readingTax Planning for the Start-up Limitation Rules

Loan to an S Corporation to Allow Tax Loss

Tax basis can limit a shareholder’s loss from an S corporation. If an S corporation has a tax loss but the shareholder doesn’t have sufficient tax basis to take the loss, the shareholder will typically have to loan money to the S corporation. This tax debt basis makes the loss allowable in the current year.…Continue readingLoan to an S Corporation to Allow Tax Loss

Tax on Payment for Being Born With Medical Condition

We can do some amazing things given the state of our science and technology. These advances lead to some interesting tax questions. The IRS recently addressed such a question in PLR 201950004. It considers whether damages paid by a fertility clinic for failing to perform a genetic test are excluded from the recipient’s income as…Continue readingTax on Payment for Being Born With Medical Condition

Reliance on an Attorney as a Defense to a Tax Crime

Reliance on advice of a tax attorney or CPA is a defense to some tax crimes. But what if a taxpayer merely consults with a tax attorney or CPA and does not actually rely on their advice? The recent United States v. Wright, No. 18-4087 (6th Cir. 2019) case addresses whether this defense is available…Continue readingReliance on an Attorney as a Defense to a Tax Crime

When an IRS Agent Makes a Misrepresentation

IRS agents interact with taxpayers. In doing so, they make misrepresentations as any other human does. Some are unintentional and some are intentional. But what is a taxpayer to do if the IRS agent makes a misstatement and it negatively impacts the taxpayer? The McRae v. Commissioner, T.C. Memo. 2019-163, case touches on this issue.…Continue readingWhen an IRS Agent Makes a Misrepresentation

Sale of Trailers Doesn’t Qualify for Installment Sale Treatment

If you buy, subdivide and sell real estate, can you seller-finance the sales and report the gain over a long period of time? The answer is generally yes, but advance planning is needed. The court addresses this in Joyner Family Limited Partnership v. Commissioner, T.C. Memo. 2019-159. Facts & Procedural History The taxpayers purchased land…Continue readingSale of Trailers Doesn’t Qualify for Installment Sale Treatment

Correcting an Erroneous Judgment for Unpaid Taxes

If the IRS gets a court judgment for unpaid taxes, can you challenge the judgment after it is entered? What if you can show that no tax is due? Can you fix the erroneous judgment after the fact? Can you just prepare corrected returns and file them? The court addresses this in United States v.…Continue readingCorrecting an Erroneous Judgment for Unpaid Taxes

Bad Debt Tax Deduction for Guarantee Payment?

If you guarantee a loan for a third party and have to make payments due to the guarantee, do you get to deduct the payment as a bad debt for tax purposes? The court addresses this in Baker Hughes, Inc. v. United States, No. 18-20585 (5th Cir. 2019) in the context of a payment made…Continue readingBad Debt Tax Deduction for Guarantee Payment?

Foreign Trust Beneficiary Liable for a Double Tax Penalty?

Can the sole owner of a foreign trust who is also its sole beneficiary be penalized twice for not filing a single Form 3520? Can the IRS choose the higher penalty for the beneficiary in this situation? In Wilson v. United States, No. 19-cv-5037 (BMC) (E.D.N.Y. 2019), the IRS argued that it could impose pick…Continue readingForeign Trust Beneficiary Liable for a Double Tax Penalty?

Sale of Long-Term Service Contracts: Capital or Ordinary Gain?

If a taxpayer sells a business that owns long-term service contracts, is the gain attributable to the contracts subject to tax at ordinary or capital gains rates? The IRS’s recent action on decision for the Greenteam Materials Recovery Facility PN v. Commissioner, T.C. Memo. 2017-122 court case deals with this in the context of a…Continue readingSale of Long-Term Service Contracts: Capital or Ordinary Gain?

Estate Plan Triggers Liability for Unpaid Taxes

Estate planning often involves transferring business interests from one generation to the next.  But what if the parent owes unpaid taxes? Can the children be held liable for the unpaid taxes? What about the surviving spouse? What if they were not aware of the steps taken to avoid paying taxes? The recent United States v…Continue readingEstate Plan Triggers Liability for Unpaid Taxes

The IRS Recent Focus on S Corp Owners

The IRS has announced several new compliance campaigns focusing on S corporations. This is needed as the audit rate for S corporation is extremely low. The most recent IRS compliance campaign focuses on shareholder stock basis issues for S corporation owners. Those who have significant S corporation losses or large distributions should take time to…Continue readingThe IRS Recent Focus on S Corp Owners

Travel Expenses Allowed for Repetitive Pattern of Travel

The IRS frequently challenges travel expenses.  These expenses have a higher substantiation requirement, which the IRS uses to disallow every expense no matter how reasonable or how certain it is that the expense was incurred.  But what if it was exceedingly certain that the expense was incurred and there is a method for computing the…Continue readingTravel Expenses Allowed for Repetitive Pattern of Travel

Records Needed for Partial Asset Dispositions

Taxpayers often overlook “partial asset dispositions.” Their tax advisers do too. This may be due to it being a depreciation issue that seems unimportant. It may also be that the partial asset disposition is a relatively new concept. Regardless, partial asset dispositions can save taxpayers quite a bit in taxes (it is a timing issue,…Continue readingRecords Needed for Partial Asset Dispositions

Voluntary Disclosure to IRS of Privileged Communication

The attorney-client privilege projects confidential communications with attorneys. It allows the attorney to avoid disclosing protected communications. But what if the attorney voluntarily discloses information and the disclosure is to the IRS about a tax matter? The court addresses this in Gaetano v. United States, No. 19-1122 (6th Cir. 2019). Facts & Procedural History This…Continue readingVoluntary Disclosure to IRS of Privileged Communication

Using Warrants to Make Future Purchases of S Corporation Stock

Can you make a gift to charity but retain the right to pull back the value of the gift in the future, and still get a charitable deduction for the gift? The court said “no” in In Re Stapley, No. 09-47699 RLE (Bankr. N.D. Cali. 2019). The failed tax shelter included an S corporation whose…Continue readingUsing Warrants to Make Future Purchases of S Corporation Stock

Can the IRS Ignore the Legal Existence of a Corporation?

If a taxpayer forms a legal entity and it is taxed as a C corporation, can the IRS disregard the legal existence of the corporation and assess the corporation’s tax to the owner? The court addresses this in Russell v. Commissioner, T.C. Memo. 2019-146. Facts & Procedural History The taxpayer filed his personal income tax…Continue readingCan the IRS Ignore the Legal Existence of a Corporation?

The Timing Trap: Failed Installment Sales

What happens if you sell an asset and are to receive payments in the future, but your accountant fails to elect the installment method? Do you have to report the full amount of the gain in the year of sale? What happens if the buyer fails to make the payments in subsequent years? The IRS…Continue readingThe Timing Trap: Failed Installment Sales

Can IRS Rely on Third Party Reports to Identify Taxable Income?

If a third party collects monies for you and send you a report reflecting the monies but the reports show too much income, should you be taxed on the higher income or what you actually received? The Ghadiri-Asli v. Commissioner, T.C. Memo. 2019-142, case addresses this. Facts & Procedural History The taxpayer is a physician.…Continue readingCan IRS Rely on Third Party Reports to Identify Taxable Income?

IRS Levy Does Not Attach to Future Payments

The IRS levy is one of the IRS’s primary methods for collecting unpaid taxes. But the levy power is not unlimited. The IRS levy can attach to some amounts held by third parties that are owed to the taxpayer. But it does not attach to future payments. The recent Gold Forever Music Inc. v. United…Continue readingIRS Levy Does Not Attach to Future Payments

M&A Finders Fee Not Deductible for Acquirer

If a company acquires another company and pays a finders fee to the party who connected the two for the sale, is the finders fee deductible by the acquirer? This question touches on whether an expense is deductible if the real benefit is to another company. The court addresses this in Plano Holding LLC v.…Continue readingM&A Finders Fee Not Deductible for Acquirer

Can the IRS Collect Gift Tax From Recipient After 14 Years?

If someone gives you property and then dies and more than ten years has passed since the gift, can the IRS sue you to collect the amount of the gift from you? Most would think the answer is a resounding “no,” as the recipient isn’t liable for unpaid gift taxes and the statute of limitations…Continue readingCan the IRS Collect Gift Tax From Recipient After 14 Years?

Avoiding State Income Tax on Part-Time Residents

Sometimes you can’t avoid paying state income taxes. This is true for those who have no ties to any state other than a state that has an income tax. But for those who have ties to multiple states, they can often structure their affairs to avoid the state income tax. This can be difficult to…Continue readingAvoiding State Income Tax on Part-Time Residents

S Corp Conversions: Watch out for Disappearing AAA

Small and medium-sized business can save quite a bit in taxes by using S corporations. But with this tax savings comes complexity. This complexity comes from how S corporations flow through profit and have the profit taxed on the individual owner’s personal tax return. The rules for tracking this are, well, lacking. Accountants are often…Continue readingS Corp Conversions: Watch out for Disappearing AAA

Final Regulations Issued: Leveraged Partnership Distributions Still Viable

The “leveraged partnership distribution” or “disguised sale” is a common tax savings technique used by real estate owners. Taxpayers pushed the envelope with these transactions by using “bottom dollar guarantees.” This led to guidance from the government making it more difficult to benefit from leveraged partnership distributions. The Treasury recently finalized regulations that say what…Continue readingFinal Regulations Issued: Leveraged Partnership Distributions Still Viable

The Broad Reach of the Economic Substance Doctrine

Congress provides tax incentives to change taxpayer behavior. If a taxpayer changes their behavior to take advantage of the incentive, they have to do so carefully. The IRS and the courts can apply the economic substance doctrine to take away the tax benefit. This doctrine can apply to more transactions than what one would consider…Continue readingThe Broad Reach of the Economic Substance Doctrine

Documenting the Sec. 199a Rental Real Estate Safe Harbor

We have previously considered the “trade or business” requirement for the Section 199a deduction. The government recently issued guidance to clarify when rental real estate activities can qualify for the deduction. While the guidance is needed, it adopts a record keeping requirement that effectively prevents most rental real estate activities from ever qualifying for the…Continue readingDocumenting the Sec. 199a Rental Real Estate Safe Harbor

Avoiding Hobby Loss Limits for Long-Term Projects

Long-term projects often lose money. They often do so for several years. This is the result of a project that needs capital to build infrastructure or to develop a new market or to capture market share. Taxpayers may be disappointed to learn that the tax losses coming from these long-term projects in the early years…Continue readingAvoiding Hobby Loss Limits for Long-Term Projects

Bad Debt Deduction for Real Estate Lender for Non-Real Estate Loan

If a taxpayer regularly makes real estate loans from their personal accounts, they would be entitled to a bad debt deduction for loans that are not repaid. But what if they venture beyond real estate loans and make a single non-real estate loan? If the non-real estate loan goes bad, can they deduct the bad…Continue readingBad Debt Deduction for Real Estate Lender for Non-Real Estate Loan

Court Addresses Tax Losses from Short-Term Rentals

Short-term rental properties are more popular than ever. Online services like Airbnb have made this possible. But how are tax losses from short-term rentals handled? Can the taxpayer use the rental losses to offset their non-rental income for tax purposes? The court addresses one aspect of these rules in Eger v. United States, 18-cv-00199-DMR (N.D.…Continue readingCourt Addresses Tax Losses from Short-Term Rentals

Court’s Take on How to Avoid the Interest Expense Limitation

Interest one pays is generally deductible for income tax purposes. For real estate owners who borrow against the value of their properties, the interest expense deduction is often one of their largest tax deductions. This tax deduction can be limited. The court in Lipnick v. Commissioner, 153 T.C. 1 highlights how one might avoid this…Continue readingCourt’s Take on How to Avoid the Interest Expense Limitation

The Importance of Accounting for C Corporation Expenses

It is important to keep accurate books and records. Accurate books and records can result in significant tax savings. This is particularly true for entrepreneurs who own more than one business. When one or more of these businesses are taxed as a C corporation, the stakes can be even higher. The Nzedu v. Commissioner, T.C.…Continue readingThe Importance of Accounting for C Corporation Expenses

IRS & the Burden to Prove Constructive Dividends

When a C corporation pays expenses for its shareholder, the payment can be subject to income tax for the shareholder as a constructive dividend. One defense is that the expenses for the C corporation were legitimate. Does the taxpayer have to prove the amount of the expenses or does the IRS? The Combs v. Commissioner,…Continue readingIRS & the Burden to Prove Constructive Dividends

Is a Taxpayer Liable for Interest if the IRS Delays an Audit?

Can the IRS fail to audit a taxpayer for several years and then, once it actually opens the audit, drag its feet for years and then charge the taxpayer interest retroactively back to the date the tax return was filed? What if that period of time happens to be, say, fourteen years? The court considers…Continue readingIs a Taxpayer Liable for Interest if the IRS Delays an Audit?

Reasonable Cause: Proving Reliance on a Tax Advisor

If you hire a competent tax advisor and end up having a late filed return, you may be able to avoid penalties for the late filing. But this is a defense. It is something that you, the taxpayer, have to prove. So how does a taxpayer prove that they relied on a tax advsior? The…Continue readingReasonable Cause: Proving Reliance on a Tax Advisor

Is Reliance on a CPA Sufficient for a Late Filed Tax Form?

The IRS often turns a deaf ear to taxpayers who miss a filing deadline due to some action or inaction by their CPA or tax preparer. This is the case for late filing tax penalties. But what about a late filed accounting method change? Is reliance on a CPA or tax preparer sufficient for a…Continue readingIs Reliance on a CPA Sufficient for a Late Filed Tax Form?

Taxpayer Cannot Recoup Attorney Travel Costs

If the IRS wrongfully denies your refund claim and you are successful in litigating the matter in court, you are entitled to recoup some of your court costs. But what about the taxpayer’s tax attorney’s travel costs? And what if the travel costs were necessary as the tax issue was complex and a tax attorney…Continue readingTaxpayer Cannot Recoup Attorney Travel Costs

Cashing a Tax Refund Check for a False Return is a Crime

Cashing a tax refund check that was triggered by filing a false tax return is a crime. It is theft of government money. Theft of government money is different than tax evasion. The recent United States v. Box, No. 18-13935 (11th Cir. 2019) court case provides an opportunity to consider the crime of theft of…Continue readingCashing a Tax Refund Check for a False Return is a Crime

CPA Penalized for Knowledge of Understatement

Sec. 6701 imposes a penalty for assisting another person in understating their tax liability. The Sec. 6701 penalty is not subject to a statute of limitations. The IRS can assess these penalties at any time, even years and decades after the fact. This can result in very large penalty assessments for those who are in…Continue readingCPA Penalized for Knowledge of Understatement

Can the IRS Get Records from Foreign Corps that do Business in the U.S.?

In CCA 2019060408545121, the IRS asked its tax attorneys whether a foreign corporation that conducts business with a limited partner in the U.S. had to produce records.  Our tax laws provide address this very topic, as noted in the CCA. The CCA serves as a reminder that failing to provide records for transactions with foreign…Continue readingCan the IRS Get Records from Foreign Corps that do Business in the U.S.?

Reporting Debt Discharged in a Court Settlement to the IRS

There are some circumstances where information has to be reported to the IRS, even though the information does not trigger a tax. But the potential problem can be that the information reporting triggers an IRS audit or other consequences. The Form 1099-C, Cancellation of Debt, form can have this effect. In PLR 201927005 the IRS…Continue readingReporting Debt Discharged in a Court Settlement to the IRS

Voluntary Sale In Advance of Forced Auction an Involuntary Conversion?

A taxpayer can generally avoid paying income tax on gain from the sale of property if the sale is an involuntary conversion. This typically involves a government act that takes or destroys the taxpayer’s property. There are a number of different types of property and takings that can qualify? But what about a local TV…Continue readingVoluntary Sale In Advance of Forced Auction an Involuntary Conversion?

Recouping Tax on Marital Wages Repaid to Employer After Divorce

If a couple files a joint return and pays tax on the income they earn, but after they divorce it turns out that one of the spouses has to repay monies received in error, can the other spouse recoup their portion of the prior tax paid on the income? The claim of right doctrine may…Continue readingRecouping Tax on Marital Wages Repaid to Employer After Divorce

Raising a Tax Issue for the First Time in Court

With tax litigation, it is often best to raise every argument possible. But what if the law seems clear on an issue and then, during the course of the tax dispute, another court issues an opinion making the law less clear? If this isn’t discovered or realized soon enough, should the taxpayer be precluded from…Continue readingRaising a Tax Issue for the First Time in Court

Does an Author Pay Self-Employment Tax on Royalties?

Taxpayers are free to structure payments for services rather than for something other than services. This can save self-employment taxes. But can a taxpayer carve out part of their service income by asserting that some part of the income is not from a business? The Slaughter v. Commissioner, T.C. Memo. 2019-65, case addresses this in…Continue readingDoes an Author Pay Self-Employment Tax on Royalties?

Is an IRS Audit Report an Informal Claim for Refund?

Amended returns generally have to be filed to recoup overpayments of tax. What counts as a refund claim is open to interpretation, as the courts have allowed a myriad of written documents to qualify. But what about the IRS report itself? If it includes a taxpayer favorable adjustment, is the report itself an informal refund…Continue readingIs an IRS Audit Report an Informal Claim for Refund?

What if the IRS Violates the Law?

What happens if the IRS violates the law? Specifically, what if the IRS assesses a penalty and attempts to collect it without first issuing the proper notice to the taxpayer? The court addresses this in Romano-Murphy v. Commissioner, 152 T.C. 62, in the context of a trust fund recovery penalty. Facts & Procedural History The…Continue readingWhat if the IRS Violates the Law?

IRS Summons and the Attorney-Client Privilege

The attorney-client privilege protects communications with a tax attorney from disclosure to third parties, such as the IRS. If the IRS discovers that a tax attorney advised a client on a transaction that wasn’t structured properly, should the IRS be able to use its power to issue an administrative summons to require the attorney produce…Continue readingIRS Summons and the Attorney-Client Privilege

LLC Cannot Use Crewman’s Exemption for Employment Taxes

Can a U.S. citizen who owns and operates a vessel outside of the U.S. avoid paying U.S. employment taxes for its crewmen by using a foreign legal entity? The court considered this issue in DAF Charters LLC v. Commissioner, 152 T.C. 14, for a single member LLC formed in the U.S. that was owned by…Continue readingLLC Cannot Use Crewman’s Exemption for Employment Taxes

Tax Litigation When the Administrative Process Failed

There are cases where the administrative process does not reach the right conclusion. There are also cases where the administrative process isn’t available or fully completed. This can happen with tax disputes handled by the IRS. When it does, does this mean that the taxpayer cannot litigate the tax dispute? The record rule comes into…Continue readingTax Litigation When the Administrative Process Failed

Non-Taxable Subsidy or Taxable Benefit?

Some payments are not subject to Federal income tax. State subsidies are an example. But what is the difference between a non-taxable subsidy and a taxable benefit? The court addresses this in Ginsberg v. United States, No. 2018-1788 (Fed. Cir. 2019), in the context of the New York state brownfield tax credit. Facts & Procedural…Continue readingNon-Taxable Subsidy or Taxable Benefit?

IRS Not Limited in Collecting Restitution Assessments

The IRS is authorized to assess criminal restitution for certain tax crimes. This process allows the IRS to collect the criminal restitution as if it was a tax. The law authorizing these collections is relatively new and evolving. The recent Carpenter v. United States, 152 T.C. 12, case highlights why it is important for those…Continue readingIRS Not Limited in Collecting Restitution Assessments

What if the IRS Loses Your Mail?

The IRS manages to lose a lot of mail. To be fair, some of the mail is likely lost before it even gets to the IRS. When this happens, can the taxpayer lose out on their rights? The court revisits this issue in Baldwin v. United States, 17-55115 (9th Cir. 2019). Facts & Procedural History…Continue readingWhat if the IRS Loses Your Mail?