IRS

During An IRS Audit, What Do The Auditors Look For?

There’s nothing more stressful than getting that audit letter in your mailbox. IRS audit is time-consuming and could be nerve-wrecking as well. Over my career, I’ve taken multiple business and individual clients through IRS audits with no adjustments made to books or tax returns. I’d like to share a few pointers from my own experience:

I got audited, but why me?

Almost all IRS agents told me the same thing: IRS has a complex algorithm that compares your tax return data with the “curve” or “pattern” they have in their system (information gathered from “big data”) and checks for reasonableness. However, I have noticed that you are more likely to get audited if you check one or more boxes from below:

  • Choppy trend: Hitting a great year, followed by a terrible one, and then hitting it out of the ballpark again - This won’t put you on the board 100% but certainly raises a red flag. Presenting a healthy and stable trend is generally recommended, unless there is genuinely an extraordinary event, for example, natural disasters, pandemics like COVID-19, etc.

  • Big top line but running a loss: Sounds suspicious already, right? Be prepared to have reasonable explanations and documentations in line to pass this one.

  • Making too much: Net income over $1mm is typically a good indicator that you’re “making too much money”. Simply put, IRS hopes there’s something in it for them to spend the time and resources on an audit. It’s just more likely for them to get something out of it if they know you have the $$$.

What do auditors look for?

  • Process walkthrough - IRS agents ask a lot of questions, which can be intimidating. What they’re trying to do here is to understand your business process - how do you get new customers? How does a lead become cash in your bank? Based on what you said, is it possible for you to miss or under-report your income? These are all important assessments being made in this part of the audit.

  • Bank activities - Does your income match all the deposits? Did all the activities foot? Was there commingling of funds between business and personal? I always advise my clients - if you don’t want IRS to open additional audits based on results from one initial audit, keep your business and personal expenses separate, and always keep a clean paper trail.

  • Major spendings - Be prepared to present documentation for major spendings and provide comments. My clients always ask me: if I don’t have the receipts, does it mean IRS won’t let me take the deduction whatsoever? The answer is, it depends. For example, if you didn’t have the receipts for $30 charged by Uber, but you have documented on your credit card statement, that this is the trip when you went to LA for a conference, accompanied with conference related plane tickets and lodging details, there’s a good chance the IRS will allow it. However, you don’t want to push the rules - we all know that Nintendo you bought serves no purpose in your jewelry crafting business.

  • Contractor payments - Definitely a big area. IRS agents typically ask for agreements with specific service terms, work reports and related documentation to help determine the legitimacy and compliance of the contractor payments. Were W9 and/or W8-BEN collected? Were Forms 1099 filed?

  • Sample tests - If your business is on the larger scale, instead of going through all transactions, it is not uncommon for the IRS agent to sample a few transactions deemed significant or representative to form an opinion on overall financial integrity. For example, they may ask you to provide PO records from key customers, POD (proof of delivery) if you sell goods, etc.

When in need, get in touch with us to consult on your situation. At Zhong & Sanchez, we provide One-Stop-Shop Tax, Finance, Accounting and HR services for Startups and Entrepreneurs. We do it all, so you can stay focused on your business. Our experience in tax and accounting will free you from back office work; our extensive knowledge with start-ups will help you grow in the most efficient way. Located in the Silicon Valley, you can reach us at 510-606-6971 or schedule your first consultation today at https://calendly.com/zhongsanchez

IRS closer to obtaining virtual currency records

U.S. taxpayers who have traded in virtual currencies such as bitcoin, but have not reported and paid tax on the income or gains from those transactions, may face the heat as the IRS continues to press for greater tax compliance in the virtual currency arena.

Some taxpayers may evade their tax obligations by concealing or otherwise failing to report their proper amount of taxable income and thus underpay their taxes, according to the IRS, and the Service has identified several tax-compliance risks associated with virtual currencies, including a lack of third-party reporting.

Tax practitioners should understand how virtual currency transactions work because their clients may already be trading in virtual currency or will be in the near future.

Documents requested by the IRS

The government has been investigating the use of virtual currency that can be converted into traditional currency for the past several years. After the IRS issued Notice 2014-21, which took the position that transactions in virtual currency were property transactions that could result in gain or loss, it then served a John Doe summons on Coinbase Inc., a San Francisco-based virtual currency exchange company, in November 2016. (A John Doe summons, which is issued under Sec. 7609(f), does not name a taxpayer because the IRS does not know the person's name.) 

Most recently, on Nov. 30, 2017, after a lengthy summons enforcement proceeding, a federal district court issued an order granting in part and denying in part the IRS's petition to enforce the summons. The court's order (Coinbase, Inc., No.17-cv-01431-JSC (N.D. Cal. 11/28/17) (order re: petition to enforce summons) requires Coinbase to produce the following documents for accounts with at least the equivalent of $20,000 in any one transaction type (buy, sell, send, or receive) in any one year during the 2013 to 2015 period:

  1. The taxpayer identification number;
  2. Name;
  3. Birthdate;
  4. Address;
  5. Records of account activity; and
  6. All periodic statements.

Once the documents are produced, the IRS will begin sifting through a vast amount of information to identify U.S. taxpayers who the IRS believes are not complying with their tax obligations. Those taxpayers may be subject to civil examinations and potentially owe tax, interest, and civil penalties. Other taxpayers with more serious issues could become subject to criminal investigation — if, for example, they have large amounts of unreported income over several years.

All of this is yet to be determined as the Coinbase case plays out. Taxpayers who think they may have exposure would be wise to take steps to comply, such as participating in the IRS domestic or offshore voluntary disclosure programs, as opposed to waiting for the IRS to catch them.

Notice 2014-21

The IRS laid the groundwork for enforcement in the virtual currency world by issuing Notice 2014-21, which provides answers to frequently asked questions (FAQs) on virtual currency, such as bitcoin. The 16 FAQs in the notice discuss the U.S. federal tax implications of transactions in, or transactions that use, virtual currency. For taxpayers trading in virtual currency, the notice is an important document to understand, and for tax professionals, the notice is a must-read. The IRS also updated its website in March 2014 to include a landing page specifically dedicated to virtual currency and providing an overview of the rules and a link to Notice 2014-21. 

The IRS's position is that virtual currency is treated as property for federal tax purposes and that general tax principles that apply to property also apply to transactions using virtual currency (Notice 2014-21, FAQ No. 1). This means that a taxpayer who receives virtual currency as payment for goods or services must, in computing gross income, include the fair market value (FMV) of the virtual currency, measured in U.S. dollars, as of the date that the virtual currency was received (FAQ No. 3).

Taxable income from buying goods or services

Suppose a U.S. taxpayer, J, located in Mountain View, Calif., performs software contracting services in 2015 for a client, M, located in the Netherlands. J emails M an $8,500 invoice for the work. Instead of sending a check from the Netherlands, M pays J for his consulting services by electronically transferring bitcoin to J's virtual currency account.  

Since the virtual currency is convertible, J cashes out and electronically transfers the funds to his personal bank account. Under Notice 2014-21, J has taxable income equal to the bitcoin's FMV on the date that J received the virtual currency from M (i.e., $8,500). The income is also probably self-employment income subject to self-employment tax (FAQ No. 10).

Taxable gain from buying, selling, or trading

In addition, other transactions using virtual currency trigger a reporting requirement. A taxpayer can have gain or loss upon an exchange of virtual currency for other property just as if a taxpayer sold property and in exchange received cash. Below is a quick summary of the rules:  

  • If the FMV of property received in exchange for virtual currency exceeds the taxpayer's adjusted basis of the virtual currency (the taxpayer's cost to purchase the virtual currency), the taxpayer has taxable gain.
  • A taxpayer has a loss if the FMV of the property received is less than the adjusted basis of the virtual currency (FAQ No. 6).

Capital gain or loss for property transactions, including those from virtual currency, is reported on Form 4797, Sales of Business Property, which is attached to Schedule D, Capital Gains or Losses, of a federal income tax return.

Adjusted basis of virtual currency

A critical aspect in dealing in virtual currency, and an important step that tax practitioners can assist their clients with, is maintaining adequate books and records to establish a taxpayer's adjusted basis of the virtual currency. A taxpayer's adjusted basis (or cost to purchase the virtual currency) determines the amount of taxable gain or loss.

If a taxpayer becomes the subject of a civil examination, the taxpayer, not the IRS, has the burden of proving cost basis, which normally is accomplished through contemporary documentary evidence. Without credible evidence, the IRS can take the position that the property received in the exchange is fully taxable because it has no basis.  

John Doe summons

On Nov. 17, 2016, the government filed an ex parte petition under Sec. 7609(h)(2) for an order permitting the IRS to serve a John Doe administrative summons on Coinbase, the San Francisco virtual currency exchange company, for information related to transactions conducted in convertible virtual currency (In re the Tax Liabilities of John Does, No. 3:16-cv-06658-JSC (N.D. Cal. 11/17/16)). The IRS sought the identity of U.S. persons who had not properly reported income from their use of virtual currency. 

A John Doe summons is a powerful tool for the government to discover the identity of individuals who may have failed to disclose all of their income (see Bisceglia, 420 U.S. 141 (1975)). Unlike a normal summons seeking information about a specific taxpayer whose identity is known, a John Doe summons seeks information about a group of taxpayers (Secs. 7609 (c)(3) and 7609(f); see also Internal Revenue Manual (IRM) §25.5.7, "Special Procedures for John Doe Summonses"). The IRS may issue a John Doe summons only after a court proceeding in which the government meets three requirements:

  1. The summons relates to the investigation of a particular person or ascertainable group or class of persons;
  2. There is a reasonable basis for believing that the person or group or class of persons may fail or may have failed to comply with any provision of any internal revenue law; and
  3. The information sought is not readily available to the IRS from other sources (Sec. 7609(f)).

Unlike a normal court hearing, where both sides submit briefs and participate in the hearing, the court decides the case based only upon a review of the government's petition and supporting documents (Sec. 7609(h)(2)). Coinbase was not permitted to appear in court or to file briefs. An important takeaway is that the government only needs to establish a reasonable basis for believing that a group or class of persons has failed or may have failed to comply with any provision of any internal revenue laws. No further showing is required.

In the Coinbase case, the government pointed to the following evidence, set forth in its pleadings, in support of its petition to enforce the summons:

  1. A report issued by the U.S. Government Accountability Office (GAO) regarding tax compliance issues relating to virtual currency;
  2. Notice 2014-21, where the IRS set forth its position that virtual currencies that can be converted into traditional currency are property for tax purposes;
  3. A second GAO report issued in May 2014 focusing on public policy challenges posed by the use of virtual currencies; and
  4. A signed declaration by an IRS senior Revenue Agent, who had gathered information regarding tax compliance issues posed by the use of virtual currency (In re the Tax Liabilities of John Does, No. 3:16-cv-06658-JSC (N.D. Cal. 11/17/16) (memorandum in support of ex parte petition for leave to serve John Doe summons)).

After reviewing the government's petition and supporting documents, on Nov. 30, 2016, the federal district court issued an order granting the ex parte petition for leave to serve a John Doe summons on Coinbase (In re the Tax Liabilities of John Does, No. 3:16-cv-06658-JSC (N.D. Cal. 11/30/16) (order granting ex parte petition for leave to serve "John Doe" summons)).

Summons enforcement proceedings

When the IRS served the John Doe summons on Coinbase, the company refused to comply, so the government filed a petition in federal district court to enforce it. On Nov. 28, 2017, after briefing and an oral hearing, the court issued an order enforcing the summons. A few observations are worth noting about the summons enforcement proceeding in federal district court:

  • The court found that the IRS summons served a legitimate purpose of investigating the reporting gap between the number of virtual currency and bitcoin users reporting gains or losses to the IRS. The court relied, in part, on the IRS's assertion that only 800 to 900 taxpayers reported bitcoin gains to the IRS during each of the relevant years.
  • However, the court ruled that the summons went beyond seeking relevant information and narrowed the scope to a limited category of documents.
  • The court's opinion provides insight into the scope and type of documents the government can obtain in a summons enforcement proceeding dealing with a virtual currency exchange company.

What to expect

The next step is for the IRS to begin sifting through the Coinbase data and identifying U.S. taxpayers who the IRS believes are not complying with their tax obligations by comparing the information received from Coinbase with information reported by taxpayers on their returns. Some U.S. taxpayers may be selected for audit.

The IRS will be looking for unreported income (e.g., gain from the sale or exchange of virtual currency based upon a review of a taxpayer's periodic account statements), and taxpayers may face, at a minimum, the civil accuracy-related penalty (a 20% penalty under Sec. 6662) and possibly the civil fraud penalty (a 75% penalty under Sec. 6663). In cases with larger amounts of unreported income over a number of years, the IRS could refer the case to IRS criminal investigation (see Fink, 1 Tax Controversies: Audits, Investigations, Trials §5.01 (2017)). 

Looking forward

The best course of action now for U.S. taxpayers who have used virtual currencies is to take steps to comply and minimize their exposure through, for example, the IRS voluntary disclosure process. Cases are harder to resolve, and the civil penalties can be greater, after the IRS contacts a taxpayer. Expect the IRS to be most interested in U.S. taxpayers who have traded in virtual currency. If a taxpayer is contacted, however, the following points are worth considering for tax professionals representing a client during a tax audit:

  1. Although the government has issued its position in Notice 2014-21 that virtual currency transactions are taxable as property, it is uncertain whether certain virtual currency transactions are actually subject to U.S. taxation. Tax professionals should carefully review the virtual currency exchange transactions, get a handle on the facts early on, and develop a defensible strategy as to the amount of unreported income.
  2. Notice 2014-21 recognizes that penalty relief may be available to taxpayers who are able to establish that the underpayment of tax is due to reasonable cause.
  3. Where the law is vague or unsettled on whether a transaction has generated taxable income, courts have found that the defendant lacked willfulness, which is a defense to tax evasion or the civil fraud penalty (Office of Chief Counsel, Criminal Tax Division, IRS Tax Crimes Handbook, p.  10 (2009), citing Harris, 942 F.2d 1125, 1131 (7th Cir. 1991) (involving payments by wealthy widower to mistresses where civil tax cases had held such payments were gifts); Garber, 607 F.2d 92, 100 (5th Cir. 1979) (novel issue of tax treatment of money received from sale of rare blood)). There is no question that taxation of virtual currency transaction is a relatively new and complex area of tax law.
  4. A good-faith misunderstanding of the law or a good-faith belief that one is not violating the law is a defense to willfulness (e.g., tax evasion or civil fraud penalty); a taxpayer simply may not have known that he or she had to report and pay tax on certain virtual currency transactions that the taxpayer had not converted into traditional currency (Cheek, 498 U.S. 192 (1991); Stadtmauer, 620 F.3d 238 (3d Cir. 2010)).

Compliance is key

Virtual currency tax cases are a new and evolving area of the law, and further developments are expected as cases begin to be worked by IRS agents and eventually wind their way through the agency and the courts. U.S. taxpayers who have traded in virtual currency would be wise to seek the advice of competent tax counsel, who can evaluate the case, explain the options, and develop a defensible strategy.  

Source: https://www.thetaxadviser.com

Current developments in S corporations

EXECUTIVE
SUMMARY

  • A binding, nonjudicial settlement agreement, where available under state law, offers a practical alternative to a probate court ruling to revise a trust's terms to comply with requirements to be a qualified Subchapter S trust.
  • An extension of time to make a "closing of the books" election upon termination of an S election may be available under Regs. Secs. 301.9100-1 and 301.9100-3, a recent IRS letter ruling demonstrates.
  • If an S corporation has accumulated earnings and profits and excess passive investment income for each of three consecutive tax years, its S election terminates. The IRS waived an inadvertent termination under the facts and circumstances presented in a letter ruling request. Other letter rulings determined that certain rental income was not passive investment income.
  • The Tax Court ruled in several cases involving S corporation shareholder basis that taxpayers claimed was created or increased by debt obligations. Other court cases involved determining whether the S corporation or its employee-shareholder was required to recognize income from providing services, the effect on basis of shareholders' income inclusion under Sec. 83(b), and allocation to a bankruptcy estate of shareholders' passthrough items.

In 2016 and 2017, courts have decided several cases involving S corporations and their shareholders. In addition, the IRS has issued guidance that should be of interest to S corporation owners. The AICPA S Corporation Taxation Technical Resource Panel offers the following summary of the court decisions and IRS guidance affecting S corporations and their shareholders that the panel believes will be of interest to tax practitioners.

Final regulations under Sec. 385


The IRS and Treasury in 2016 issued proposed regulations under Sec. 385 addressing when a purported debt instrument would be recharacterized as equity for income tax purposes.1These proposed regulations caused significant concerns from an S corporation perspective because their effect on a corporation's ability to satisfy the small business corporation requirements2 was unclear. Specifically, the proposed regulations raised concerns about whether the recharacterization of a purported debt instrument as equity would cause the issuing corporation to be treated as having more than one class of stock and/or cause the holder to be treated as a shareholder of the issuing corporation. However, in the final and temporary regulations issued in October 2016, S corporations are exempt from all aspects of these regulations.3

Reforming a trust to qualify as a qualified Subchapter S trust


In two private letter rulings,4 the IRS ruled that a trust was a qualified Subchapter S trust (QSST) following its reformation pursuant to a binding, nonjudicial settlement agreement.

Under the facts of the letter rulings, the terms of a trust that provided for discretionary distributions to the descendants of the primary beneficiary during the primary beneficiary's lifetime were reformed pursuant to a binding, nonjudicial settlement agreement so that the QSST requirement limiting distributions to the current beneficiary during the beneficiary's lifetime would be satisfied.5 Under the laws of the state that governed the trust, interested parties could enter into a binding, nonjudicial settlement agreement with respect to the validity, interpretation, or construction of the terms of the trust that would be final and binding on the trustee, all current and future beneficiaries of the trust, and all other interested persons, as if ordered by a court.

These letter rulings highlight a practical alternative to a probate court ruling for modifying the terms of a trust to qualify it as a permissible S corporation shareholder. However, it is important to note that modifications to a trust, whether via a nonjudicial settlement agreement or a probate court ruling, will likely not be given retroactive effect for purposes of the trust's qualifying as an S corporation shareholder, even if effective retroactively under applicable state law.6

Extension of time granted to file a 'closing of the books' election


If an S election terminates on a date other than the first day of the corporation's tax year, an "S termination year" results, consisting of an "S short year" and a "C short year."7 Unless a closing of the books is required, the corporation's items of income, gain, loss, deduction, credit, etc., are allocated between the S short year and the C short year on a daily, pro rata basis.8 However, a corporation may elect to not have the pro rata allocation rule apply and instead assign the items of income, gain, loss, deduction, credit, etc., for the S termination year to the S short year and the C short year under normal tax accounting rules (the "closing of the books election").9 The election is made by filing a statement with the corporation's return for the C short year.10 In a recent letter ruling,11 the IRS granted the taxpayer an extension of time to file a closing-of-the-books election pursuant to Regs. Secs. 301.9100-1and 301.9100-3.

Passive investment income (Secs. 1362(d)(3) and 1375)


S election termination from excess passive investment income was inadvertent

Under Sec. 1362(d)(3), if, for three consecutive tax years, an S corporation has accumulated earnings and profits at the close of each tax year and has excess passive investment income12 for each tax year, then the corporation's S election terminates at the beginning the first day of the first tax year following the third consecutive tax year. Under Sec. 1375(a), if an S corporation has accumulated earnings and profits at the close of a tax year and has excess passive investment income for the tax year, a tax is imposed on the corporation's net passive investment income.

In Letter Ruling 201710013, the IRS determined that the termination of the taxpayer's S election under Sec. 1362(d)(3) was inadvertent, even though the taxpayer had paid the tax imposed under Sec. 1375(a) for three consecutive tax years. The taxpayer represented that it was aware that having excess passive investment income could subject it to tax but was unaware that this could cause a termination of its S election. To obtain the ruling, the taxpayer agreed to distribute its accumulated earnings and profits by making a deemed dividend election under Regs. Sec. 1.1368-1(f)(3).

ObservationNote that the deemed dividend election under Regs. Sec. 1.1368-1(f)(3) may be made on a timely filed original or amended return. Thus, provided that the period of limitation on assessment has not closed for the third consecutive tax year in which a taxpayer has accumulated earnings and profits and excess passive investment income, the terminating event may be avoided by making this election on an amended return to distribute all of the corporation's accumulated earnings and profits.

Sharecropping revenue and rental income are not passive investment income

The IRS ruled in Letter Ruling 201722019 that sharecropping revenue and rental income were not considered passive investment income under Sec. 1362(d)(3)(C)(i).

Taxpayer X was engaged in a farming arrangement with another taxpayer for sharecropping purposes whereby direct expenses including processing expenses were allocated based on the percentage of crops to which each was entitled. Taxpayer X paid all utilities, maintenance, box rent, and inspection fees and was responsible for all decisions regarding the type of crops planted and marketing efforts. In a subsequent year, a new lease arrangement was signed, where X's expenses were a percentage of rental income within a fixed range, but all property taxes were to be paid byX.

The IRS held that, based on the facts and representations made, the revenue received under the sharecropping agreement and the rental income under the lease arrangement were not considered passive investment income under the rules in Sec. 1362(d), but the rental activity could still be subject to the passive activity rules of Sec. 469.

Rental income did not constitute passive investment income

The IRS ruled in Letter Ruling 201725022 that rental income received by a corporation intending to be treated as an S corporation did not constitute passive investment income for purposes of Sec. 1362(d)(3)(C)(i).

The taxpayer owned a series of commercial buildings that were leased for medical offices and support activities. The taxpayer contracted with an independent leasing agent to provide assistance with obtaining, negotiating, and renewing leases, which required significant time and attention. The taxpayer had a standard lease agreement with its tenants indicating that the landlord was responsible for maintenance and repair activities, including building systems, lighting, lawn care, walkways, and utilities. Furthermore, the taxpayer represented that these activities were performed daily by the taxpayer, its employees, its agent, and the agent's employees. The IRS ruled that the rental income received from these activities was not passive income for purposes of Sec. 1362 but could still be subject to the passive activity loss rules under Sec. 469.

Shareholder basis


In Hargis,13 the Tax Court ruled that the taxpayer, an S corporation shareholder, failed to establish that he had sufficient basis in S corporation stock and debt to deduct the losses allocated to him from the S corporation. The taxpayer relied on his position as "co-borrower" on notes from outside lenders to the S corporation and notes from related business entities to the S corporation to support his claim of sufficient basis to claim the losses.

The court determined that the loans were made directly between the lenders and the S corporation and that the S corporation was not directly obligated to the shareholder. The court noted that none of the proceeds from the loan agreements were advanced to the shareholder but rather were paid directly to the S corporation. In addition, the shareholder was not called upon to make any payment on the notes as a co-borrower, and he was not looked to by the lenders as the primary obligor on the notes. Without a direct indebtedness from the S corporation to the shareholder, the court declined to recognize basis and disallowed the lossdeductions.

The Franklin14 case is similar to Hargis in that the taxpayer was the sole shareholder of an S corporation, and he personally guaranteed the debt of his S corporation to an outside lender. Unlike Hargis, however, the shareholder in Franklin was required to make payment to the lender on the guaranteed debt when the S corporation defaulted. The Tax Court in Franklin accepted evidence that the lender did seize and sell property of the shareholder as payment on the debt of the S corporation.

The Tax Court acknowledged that the shareholder increased his basis in the S corporation by the amount of the actual payment made under his debt guarantee. The additional basis allowed the shareholder to deduct tax losses allocated to him from the S corporation. However, no deduction was allowed in another year where the shareholder had claimed a loss but the corporation had not filed a return and there was no evidence as to the loss or anybasis.

Another debt basis case was Phillips,15 in which a 50% shareholder guaranteed debts of an S corporation. The corporation defaulted on loans, and the creditors sued the guarantors and obtained a judgment against the taxpayer. The taxpayer increased her basis for the amount of the judgments in the year that the courts awarded them to the creditors. However, she had not paid any of the judgments, and the IRS and Tax Court would not allow her to claim basis until she made payments.16

Income earned by shareholder, not S corporation


In Fleischer,17 at issue was whether an S corporation or its shareholder/employee earned income from the services provided by the shareholder/employee.

The taxpayer provided professional services to customers in exchange for commissions and fees that he assigned to his wholly owned S corporation. The taxpayer was then paid a salary from the S corporation, the remaining net income or loss of the corporation was allocated to him, and he received cash distributions.

The Tax Court's opinion in Fleischer notes a first principle of income tax: that "income must be taxed to him who earned it,"18 or, more specifically, to the person "who controls the earning of the income."19 The court noted that for a corporation, and not its service-provider employee, to be the controller of the income, two elements must be found:

  1. The individual providing the services (to the customer) must be an employee of the corporation whom the corporation can direct and control in a meaningful sense; and
  2. There must exist between the corporation and the person or entity using the services (customer) a contract or similar indicium recognizing the corporation's controlling position.

Under the facts of the case, the shareholder, in his personal capacity, entered into a contract with an unrelated party prior to forming the S corporation, and the contract indicated that the shareholder's relationship with the unrelated party was that of an independent contractor. Subsequent to the formation of the S corporation, the shareholder entered into a contract with another unrelated party in his personal capacity. There were no addendums or amendments to either of these contracts requiring the unrelated parties to begin paying the S corporation instead of the shareholder or to recognize the S corporation in any capacity.

The Tax Court held that there was no indicium for the unrelated parties to believe that the S corporation had any control over the shareholder, and therefore, the shareholder, not the S corporation, should have reported the income received under the contracts.

Inclusion of income under Sec. 83(b) creates basis for distribution


Although Austin 20 is probably most notable as an economic substance case, one of its issues involved the taxability of a "special dividend" to an S corporation's shareholders. The Tax Court determined that the S corporation "was always an S corporation" and had no accumulated earnings and profits. Thus, the "special dividend" to its shareholders qualified as a distribution under Sec. 1368(b) and was excluded from the shareholders' taxable income to the extent the distribution did not exceed their stock basis.

The shareholders had relied on certain promissory notes issued as payment for their shares to provide basis and argued that the distribution did not exceed basis. The court found that the notes lacked economic substance and rejected the argument that the shareholders had additional basis. However, as a result of other rulings in the case, the shareholders recognized income under Sec. 83(b) with respect to their shares of the S corporation's stock, increasing their basis in the stock. This increase was sufficient to absorb the distribution so that the distribution was tax-free under Sec. 1368(b).

Bankruptcy estate allocated S corporation income for entire tax year


Under Sec. 1377, generally, an S corporation must allocate its income and other tax items to its shareholders on a per-share/per-day basis. In Medley v. Citizens Southern Bancshares,21two shareholders in the same S corporation transferred their shares to bankruptcy estates in early 2014. Neither shareholder elected to split his own tax year between the pre- and post-petition period under Sec.1398(d)(2). The corporation was profitable in 2014. The trustee allocated income between the shareholders and the estates based on the number of days each shareholder had held the stock. However, the court determined that Sec. 1398(e)(1) entitled the bankruptcy estate to all of the debtor's income or loss from the bankruptcy date forward. Because income does not pass through from an S corporation to a shareholder until the final day of the corporation's tax year, and the estates were the owners of the stock on that final day, all of the debtors' passthrough items for 2014 would pass through to the estates. The Medley case followed the reasoning in Williams,22 in which a shareholder who had transferred his stock to a bankruptcy estate attempted to benefit from a portion of the S corporation's losses for the year.

Inadvertent invalid QSub election highlights trap for the unwary


It has become increasingly common for an S corporation to restructure in connection with a sale or a third-party investment. A common form of this restructuring is for the S corporation's shareholders to form a new corporation (Newco), to which the stock of the S corporation (Oldco) is contributed. A qualified Subchapter S subsidiary (QSub) election is then made for Oldco, effective as of the date of contribution. Shortly after the contribution, Oldco is converted to a limited liability company (LLC) under state law. These steps are generally intended to qualify as a reorganization under Sec. 368(a)(1)(F). An unrelated party then purchases interests of the Oldco LLC or invests in it.

In Letter Ruling 201724013, the taxpayer implemented this type of restructuring; however, the QSub election for Oldco was not filed until after Oldco had been converted to an LLC under state law. Because Oldco did not satisfy all of the QSub requirements under Sec. 1361(b)(3)(B) at the time that the QSub election was filed for it, the QSub election was invalid. The IRS granted a waiver of the inadvertent invalid QSub election under Sec.1362(f).  

Footnotes

1 REG-108060-15.

2 Secs. 1361(b) and (c) and associated regulations.

3 T.D. 9790.

4 IRS Letter Rulings 201614002 and 201614003.

5 See Sec. 1361(d)(3).

6 See Rev. Rul. 93-79.

7 Sec. 1362(e)(1).

8 Sec. 1362(e)(2).

9 Sec. 1362(e)(3).

10 Regs. Sec. 1.1362-6(a)(5).

11 IRS Letter Ruling 201706013.

12 Passive investment income is excessive if it constitutes more than 25% of the corporation's gross receipts (Sec. 1362(d)(3)(A)(i)(II)).

13 Hargis, T.C. Memo. 2016-232.

14Franklin, T.C. Memo. 2016-207.

15 Phillips, T.C. Memo. 2017-61.

16 The years involved predated amendments to Regs. Sec. 1.1366-2 discussed in "Final Regulations Under Sec. 385" above, so there was no discussion of whether the arrangement created a bona fide debtor-creditor relationship between the S corporation and theguarantors.

17 Fleischer, T.C. Memo. 2016-238.

18 Lucas v. Earl, 281 U.S. 111 (1930).

19 Quoting Johnson, 78 T.C. 882 (1982), aff'd, 734 F.2d 20 (9th Cir. 1984).

20 Austin, T.C. Memo. 2017-69.

21 Medley v. Citizens Southern Bancshares, No. 13-12371 (Bankr. M.D. Ala. 5/17/16).

22 Williams, 123 T.C. 144 (2004).

Source: https://www.thetaxadviser.com/