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Company Vehicles, Cell Phones, and Office Snacks: What’s Actually Tax-Free for Employees

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Have you ever had to explain to a client that the $35 gift card they gave each employee for the holidays must be reported as taxable compensation, but the $35 holiday ham they gave last year was completely tax-free? Welcome to the world of fringe benefit taxation, where seemingly identical gestures of employee appreciation can produce dramatically different tax consequences.

This counterintuitive example comes from Episode 18 of the Tax in Action podcast, where host Jeremy Wells, EA, CPA, continues his deep dive into IRC Section 132’s fringe benefit provisions. Building on a previous episode discussing no-additional-cost services and qualified employee discounts, this episode covers two benefit categories that touch nearly every business with employees: working condition fringes and de minimis fringe benefits.

Many employers want to provide benefits to their workforce, but the line between tax-free perks and reportable compensation often comes down to surprisingly specific details. Understanding these distinctions helps tax professionals guide clients toward meaningful benefits without triggering unexpected tax consequences.

When structured correctly, these benefits are deductible for the employer and excludable from the employee’s taxable compensation. Get the details wrong, and what was intended as a thoughtful perk becomes reportable wages subject to income, employment, and state taxes.

Working Condition Fringes Help Employees Do Their Jobs Better

The concept behind working condition fringes is straightforward. If an expense would be deductible under IRC Section 162 (ordinary business expenses) or Section 167 (depreciation) had the employee paid for it personally, the employer can provide that benefit tax-free. Some common examples include company vehicles for service technicians, professional development courses, business travel, and other things employees genuinely need to perform their jobs effectively.

But practitioners need to pay close attention to ensure the benefit relates specifically to that employee’s role with that employer. As Wells explains, if the expense instead supports outside professional activities, such as consulting privately, serving on an external board, or running a separate venture, the employer’s payment doesn’t qualify as an excludable working condition fringe. The employer would essentially be subsidizing something that benefits the employee’s outside activities rather than their own business operations.

Who Counts as an “Employee” (And Who Doesn’t)

The definition of “employee” for working condition fringes is broader and narrower than you might expect. It includes current employees, partners performing services for a partnership, directors of the employer, and even independent contractors performing services for the employer. This expanded definition allows businesses to provide qualifying benefits across different working relationships without triggering taxable compensation.

However, the definition is more restrictive than what applies to other fringe benefit categories. Former employees, spouses, and dependents can qualify for no-additional-cost services and qualified employee discounts discussed in Episode 17, but don’t make the cut for working condition fringes.

One additional group does qualify: bona fide volunteers at nonprofit organizations can receive working condition fringes without it being treated as compensation. This provides helpful flexibility for tax-exempt entities, though Wells emphasizes that understanding what organizations can provide to volunteers without converting them to compensated workers requires careful attention to the rules.

No Discrimination Rules Apply

Unlike many benefit programs, working condition fringes come with no nondiscrimination requirements. An employer can provide a company vehicle to one employee while not offering similar benefits to others. Highly compensated employees can receive working condition fringes that aren’t available to rank-and-file workers. This flexibility allows businesses to target these benefits where they’re most needed operationally.

Substantiation Requirements Still Matter

The absence of nondiscrimination rules doesn’t mean working condition fringes don’t have documentation requirements. If IRC Section 274 imposes strict substantiation requirements on a particular type of expense, those same requirements apply when the expense is provided as a working condition fringe.

Wells points to club memberships as a prime example. IRC Section 274(a)(3) disallows deductions for membership dues in clubs organized for business, pleasure, recreation, or other social purposes, such as country clubs, chambers of commerce, civic organizations, and similar groups. When clients argue these memberships generate business connections, Wells notes “just because something seems like it should be deductible, or it seems unfair that it’s not deductible, that’s just simply what the law says.”

An employer can still pay for such memberships, but they must include the value in the employee’s compensation and deduct it or exclude it from compensation and forgo the deduction entirely.

When providing cash advances for working condition fringes, employers must require employees to use the cash for specific deductible activities, verify correct use with receipts, and return any unspent cash. This differs significantly from de minimis fringes.

Getting the Details Right with Company Vehicles

Employer-provided vehicles are a common working condition fringe benefit. We’re not talking about business owners using vehicles for personal transportation, but true company vehicles like the trucks driven by HVAC technicians, the vans operated by plumbers, and vehicles used by pest control professionals.

The excludable portion is the total annual value of the vehicle multiplied by the percentage of business-use miles. “Even though it’s company owned, there still needs to be a written, contemporaneous mileage log,” Wells says, emphasizing a critical point. Digital tracking counts, but the documentation must exist.

When an employee keeps the vehicle overnight to make an early morning service call, that commute home and back to work counts as personal use. The substantiation requirements don’t relax simply because the employer holds the title.

If multiple employees share vehicles throughout the year, their combined legitimate business mileage counts in both the numerator and denominator of the business-use calculation. But if specific employees use designated vehicles during identifiable periods, the organization must maintain records separately.

Other Working Condition Fringes

Product testing is another excludable category with specific requirements. Employers must limit product availability to the testing period, require return of products afterward, and collect detailed employee reports. Notably, directors and independent contractors don’t qualify for this particular exclusion, so employers must report test products provided to them as compensation.

Job-related education qualifies as a working condition fringe when it meets requirements under IRC Section 127. Wells devoted Episode 7 entirely to deductible education costs, which provides deeper guidance on this topic.

Business travel expenses, including flights on employer-provided aircraft, can be excluded when legitimately deductible. But personal elements, such as tickets for children, personal destinations, or accompanying family members without documented business purpose, are includable in income.

For clients in higher-risk environments, enhanced security for company vehicles can qualify as working condition fringes. The key is documented specificity: general safety concerns don’t suffice. There must be evidence of actual threats, such as death threats, kidnapping risks, or recent violent incidents, and security must be part of a comprehensive 24-hour protection program.

De Minimis Fringe Benefits: When “Too Small to Count” Actually Counts

While working condition fringes help employees perform their jobs, de minimis fringes address the smaller perks that boost morale and show appreciation. The standard seems simple: if a benefit’s value is so small that tracking it would be unreasonable or administratively impracticable, employers can provide it tax-free.

But don’t let “too small to count” suggest this category operates without rules. The de minimis standard contains specific requirements, and one absolute prohibition that catches many employers off guard.

The Individual Employee Test

Frequency matters when determining whether a benefit qualifies as de minimis, and the analysis focuses on each individual employee. “Providing a daily meal to a single employee is not a de minimis fringe benefit with respect to that employee,” Wells explains, “even though if we were just looking at the number of meals provided annually to all employees, it might be a relatively small number.”

The exception comes when tracking individual frequency becomes administratively difficult. Wells offers the copying machine example. If an employer ensures at least 85% of use is for business purposes, any personal use qualifies as de minimis. Nobody expects employers to count every personal page, so these rules eliminate that administrative burden.

The Absolute Cash Equivalent Prohibition

Here’s where many well-intentioned employers stumble: cash and cash equivalents are never excludable as de minimis fringes. No exceptions. The rationale is, it’s never administratively impracticable to account for cash.

This creates counterintuitive outcomes that confuse clients. The holiday ham or turkey is the textbook de minimis fringe, literally cited by Congress when explaining IRC Section 132. But when one employer switched from holiday hams to $35 gift certificates for local grocery stores, the IRS ruled those certificates were cash equivalents and thus no longer excludable.

“Even though in terms of frequency and amount, it might appear de minimis, I can specifically and administratively identify how much was spent so that is never going to be excludable,” Wells emphasizes.

Office Snacks and the TCJA Changes

Coffee, donuts, and soft drinks in the office are another classic de minimis fringe benefit. So are occasional meals or meal money provided specifically for employees working overtime, with emphasis on “occasional” and the overtime connection. Company parties, picnics, and group meals (including guests) also qualify.

These categories generated confusion following the 2017 Tax Cuts and Jobs Act. “I saw a lot of social media posts claiming the legislation made office snacks, donuts, and soft drinks nondeductible and includable. Neither one of those is true,” Wells says, clarifying an important misconception.

What actually changed is pre-TCJA, these items were 100% deductible. Post-TCJA, office snacks and occasional meals became 50% deductible. They’re still deductible, just at half the rate. They remain fully excludable from employee compensation.

What did become nondeductible after 2025 are expenses for employer-operated eating facilities—essentially cafeterias that charge employees for food. But basic office snacks are 50% deductible for employers and still tax-free for employees.

Employer-Provided Cell Phones

Cell phones occupy an interesting position, potentially qualifying under both working condition and de minimis rules. The key is why the employer provides the phone.

If they provide it so the employee can be on-call outside normal hours, then the business use qualifies as a working condition fringe and personal use as de minimis. As a result, the entire value is excludable for the employee and deductible for the employer.

However, phones provided to boost morale or included in employment contracts as compensation don’t qualify. The phone must serve the employer’s operational need for employee availability.

Holiday and Special Occasion Gifts

Employers can provide occasional, non-extravagant gifts for holidays, birthdays, achievements, illnesses, or family crises as excludable de minimis fringes. Wells notes these should be “one off or occasional, maybe annual. Probably not more often than that.”

But the cash equivalent prohibition applies fully here. A $35 gift basket is excludable. A $35 gift card to the employee’s favorite restaurant must be included in compensation. Same dollar amount, same thoughtful intent, completely different tax treatment.

Common Pitfalls and Non-Excludable Benefits

Wells identifies several benefits that commonly trip up employers who assume they’re tax-free:

  • Season tickets to sporting or theatrical events cross the line into reportable compensation, though a single occasional ticket might qualify as de minimis.
  • Commuting use of employer-provided vehicles remains personal use that must be tracked and potentially reported, even for company-owned vehicles used primarily for business.
  • Private country club or athletic facility memberships don’t qualify as excludable fringes, despite potential business networking value.
  • Group term life insurance on a spouse or child creates taxable compensation, as only coverage on the actual employee qualifies for favorable treatment.
  • Personal use of employer facilities like a beach condo or hunting lodge generates reportable income. Wells notes clients often want to rent cabins for “strategic planning” retreats, but “it would be a stretch to say that was an actual business expense.”

The Documentation Imperative

Throughout the episode, Wells emphasizes that “documentation is key.” Even without nondiscrimination requirements, written policies and records protect both employers and employees.

Best practices include:

  • Maintaining detailed records of what benefits were provided, when, and to whom
  • Tracking benefit values even for seemingly trivial items
  • Ensuring you’ve satisfied substantiation requirements under IRC Section 274
  • Documenting eligibility criteria in writing

“It’s always best practice to clearly document in writing who earns what kinds of benefits,” Wells advises, “even if there are no nondiscrimination rules for the particular kind of benefit.”

Turning Fringe Benefit Rules Into Client Value

Working condition fringes and de minimis benefits offer employers meaningful ways to support their workforce beyond traditional compensation. Company vehicles enable service technicians. Cell phones keep employees connected. Office coffee makes the workplace pleasant. Holiday gifts acknowledge contributions. When structured correctly, these benefits are deductible for employers and invisible on employee W-2s.

For tax professionals, mastering these distinctions creates immediate value for business clients. Every employer wants to provide meaningful benefits. Guiding them toward tax-efficient structures while avoiding pitfalls demonstrates expertise that justifies advisory relationships.

Listen to the full Tax in Action episode for Jeremy Wells’ complete analysis, including additional examples and nuances not covered here.

The Math Behind Tax-Free Employee Discounts That Most Businesses Get Wrong

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Picture an airline employee boarding a flight home after visiting family, slipping into an empty seat at the last minute without paying a dime. Is this a tax-free perk or unreported income? The answer hinges on one crucial detail that could mean thousands of dollars in tax liability, whether that seat was reserved or simply excess capacity.

In this first episode of a multi-part series on tax-free employee benefits, Tax in Action host Jeremy Wells, EA, CPA, breaks down the complex world of no-additional-cost services and qualified employee discounts under IRC Section 132. As Jeremy explains, “Employers are constantly trying to figure out ways to encourage either prospective employees to want to come work for them, or for current employees to want to stay.” These benefits have become essential recruiting tools, yet their tax-free status depends on following precise technical requirements.

The Starting Point: Everything Is Taxable Unless…

Jeremy begins with a reality check that sets the stage for everything that follows. “IRC 61(a)(1) includes in compensation for services, commissions, fringe benefits, and similar items in gross income,” he emphasizes. “So in other words, if you get some sort of fringe benefit from your employer, it’s taxable unless there is some specific exception in the code.”

This means every perk, discount, or free service an employer provides is taxable compensation by default. Section 132 provides specific exceptions, but only if employers and employees follow the rules. Miss one requirement, and that tax-free benefit becomes taxable wages subject to withholding, penalties, and interest.

This episode focuses on two of the most common Section 132 benefits: no-additional-cost services and qualified employee discounts.

No-Additional-Cost Services: The Excess Capacity Exception

The concept seems simple enough: if providing a service to an employee doesn’t cost the employer anything extra, the employee can receive it tax-free. But as Jeremy explains, employers have to meet multiple requirements.

A no-additional-cost service must be “one provided to an employee for personal use,” Jeremy notes. “It’s ordinarily offered for sale to customers, and it incurs no substantial additional cost or foregone revenue when provided to the employee.”

The Reservation Problem

Jeremy returns repeatedly to airline examples because they perfectly illustrate the distinction between acceptable and problematic benefits. When discussing an empty airline seat, he explains, “The airline wasn’t going to sell that ticket anyway. So the airline isn’t losing anything. It’s not paying any more than it had to to add one more passenger to that flight.”

This is true excess capacity. Once the plane door closes, that empty seat has no value so letting an employee use it costs nothing.

But Jeremy warns about a critical limitation. “Employers can’t exclude reserved services.” If an employee reserves a seat while customers can still book the flight, “that airline potentially loses revenue if a customer wants to book that flight but can’t because the employee took the last seat.”

The employee could still take that reserved seat without paying, but “the airline would need to add the value of that ticket to the employee’s compensation as taxable income as part of the employee’s wages.”

Calculating Substantial Additional Cost

Determining whether a service incurs “substantial additional cost” requires careful analysis. “The employer has to include the cost of labor incurred in providing the service,” Jeremy explains. For modern service businesses, this can be challenging. While a manufacturer can easily track labor hours per widget, service businesses often struggle to allocate labor costs to specific services.

Jeremy offers some relief through the concept of “incidental services.” If a service is secondary to normal operations, it “generally doesn’t incur substantial additional cost.” This gives employers a near-safe harbor for ancillary services.

However, there’s a catch: “The employer incurs substantial additional cost if the employer or its employees spend a substantial amount of time providing the service to employees.” The vagueness is frustrating. “We don’t really get more detail than that,” Jeremy points out.

Reciprocal Agreements: Trading Services Tax-Free

One interesting provision allows unrelated companies to trade services. “An employer has to have an agreement with an unrelated other employer,” Jeremy explains, outlining three requirements:

  1. It must be a written reciprocal agreement
  2. The employee could exclude the value if their own employer provided it
  3. Neither employer can incur substantial additional cost

Jeremy emphasizes a crucial restriction. “If there are any payments involved between the two companies, then that is by definition a substantial additional cost and the entire agreement breaks down.” The exchange must be pure barter—services for services, no money changing hands.

Qualified Employee Discounts: Different Rules for Products and Services

While no-additional-cost services focus on excess capacity, employee discounts involve mathematical calculations that vary dramatically between services and products.

The 20% Rule for Services

For services, there is a clear bright-line test: “A discount on a service can’t exceed 20% of the price offered by the employer to customers.”

Using a simple example, “If your business provides a particular service to its customers for $100, then you can offer that same service to your employees for no less than $80” without tax consequences. Charge $70, and that extra $10 becomes taxable wages.

Gross Profit Calculations for Products

Product discounts follow a completely different formula. “The discount can’t exceed the gross profit percentage on the price offered by the employer to customers,” Jeremy explains. This requires complex calculations.

Jeremy walks through a practical example using a lawn equipment retailer offering employee discounts on push mowers. The store can’t just pick one model; it must aggregate. “Let’s look at the aggregate sales price. So of all of our push lawn mowers, what is the aggregate sales price of all of them?”

The calculation averages across the entire product line. “Some of them are going to be cheap. Some of them are going to be expensive. Some of them are going to be top of the line.” The employer calculates both average selling price and average cost to determine the gross profit percentage and that becomes the maximum tax-free discount.

The 35% Group Discount Rule

If a business regularly offers discounts to customer groups, such as seniors or military, and those sales comprise at least 35% of total sales, the discounted price becomes the baseline. “We’re trying to avoid inflating the price to act like we can afford a bigger discount for our employees,” Jeremy explains.

When multiple discount groups exist, employers can “choose the most common discount, the one producing the largest share of total discounted sales as the benchmark. Or if there’s a tie, it can average between them.”

What Can’t Be Discounted

Jeremy identifies surprising exclusions, including real estate, buildings, and land, and personal property usually held for investment, such as securities, commodities or currencies.”

Even businesses that primarily deal in these items, such as real estate brokerages and securities firms, cannot offer tax-free employee discounts on their main products.

Unlike no-additional-cost services, Jeremy makes clear that employee discounts have a major limitation. “You can’t create a reciprocal arrangement with another company to provide discounts on goods or services.”

The Compliance Framework: Who Qualifies and How to Document

Beyond the mathematical requirements are administrative challenges that can transform simple perks into compliance nightmares.

Nondiscrimination Requirements

Highly compensated employees—those earning over $160,000 in 2025 or owning 5% or more of the business—face special restrictions. They “can exclude no additional cost services, but only if the employer offers that service on substantially the same terms to each member of a group of employees.”

Jeremy provides a practical example of acceptable classification. “Once a new employee works for the business for at least six months or one year, then that employee is now eligible for the fringe benefit.” This creates an objective standard applying equally to all compensation levels.

Line-of-Business Limitations

This requirement emerged from the corporate consolidation era. “You started seeing businesses merging and acquiring other businesses,” Jeremy observes, “and pretty soon a business didn’t offer just one type of good, it might offer ten, 20, or 50 different kinds.”

The rule is, employees can only receive tax-free benefits for goods or services related to their line of business. Jeremy offers a clear example: “A bank can’t provide discounted apparel or groceries to its employees if it doesn’t also primarily sell clothing and groceries to its customers.”

However, employees supporting multiple divisions qualify more broadly. Administrative staff, IT professionals, and other infrastructure workers who benefit multiple lines of business can receive benefits from any division they support, even indirectly.

The Outdated Classification System

Determining lines of business relies on the Standard Industrial Classification system, which Jeremy notes was developed in 1938 and hasn’t been updated since 1974. Many modern businesses operate in industries that didn’t exist when these codes were created. While the Treasury proposed updating to the modern NAICS system in August 2024, employers must still navigate using pre-internet classifications.

Documentation Requirements

Jeremy concludes with essential documentation advice:

  • Document employees’ regular work to prove line-of-business compliance
  • Confirm services/products are offered to customers ordinarily
  • Quantify any costs or foregone revenue for no-additional-cost services
  • Calculate and document gross profit percentages
  • Maintain pricing records from when benefits were provided

“Document the terms of the benefit, ideally in writing,” Jeremy emphasizes, suggesting inclusion in employee manuals.

Looking Ahead: More Benefits to Come

Section 132 benefits reveal how simple concepts, such as free services and employee discounts, become complex compliance exercises requiring careful calculation and documentation. Yet for employers competing for talent, mastering these rules is essential for offering competitive compensation packages without triggering unexpected tax consequences.

Jeremy promises to continue this series in the next episode: “We’ll keep looking at Section 132 with working condition fringe benefits and de minimis fringe benefits.”

For tax professionals advising clients or business owners designing benefit packages, understanding these requirements is about maximizing value for employees while avoiding costly mistakes. The difference between a valued perk and a tax liability often lies in a single detail, such as whether a seat was reserved or whether discounts were properly calculated.

Listen to the full episode of Tax in Action to hear Jeremy break down each requirement with the clarity that makes complex rules immediately applicable in your practice.

The IRS Can Hit Your Clients With Criminal Charges for Bad Bookkeeping (And Most Tax Pros Don’t Know It)

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If you’ve ever received a shoebox full of receipts from a client or struggled with QuickBooks files where half the expenses are labeled “miscellaneous,” you know the frustration. But according to Jeremy Wells, EA, CPA, in this episode of Tax in Action, poor recordkeeping isn’t just a workflow problem. It’s a legal violation that could cost your clients thousands in penalties.

Most tax professionals treat recordkeeping like a suggestion. But it’s actually a federal requirement with serious consequences, including a 20% penalty on underpaid taxes and even potential criminal charges. Understanding these requirements can transform your practice and create new revenue opportunities.

Your clients are breaking the law (and they don’t know it)

Wells starts with a section of the tax code that most practitioners overlook. IRC Section 6001 doesn’t suggest or recommend. It requires taxpayers to “keep such records, render such statements, make such returns, and comply with such rules and regulations as the Secretary may from time to time provide.”

The Treasury regulations spell it out even more clearly. Taxpayers must keep “permanent books of account or records, including inventories, as are sufficient to establish the amount of gross income, deductions, credits, or other matters required to be shown by such person in any return.”

“The way I read this,” Wells explains, “you as a taxpayer, in order to file a tax return, need to have permanent books and records you can rely on in order to justify and substantiate any amount of gross income, deductions, credits, or anything else that you’re putting into that return.”

Here’s what catches many people off guard: tax returns themselves don’t prove anything. In Wienke v. Commissioner (T.C. Memo 2020-143), the Tax Court established that returns are “merely statements of claims and are not considered evidence of the claims themselves.” The real evidence must come from the taxpayer’s books and records. So when your client thinks their signed tax return proves their income to a lender, they’re wrong. Without proper records backing it up, that return is just a piece of paper with numbers on it.

The penalties for inadequate recordkeeping can devastate a small business. Section 6662 imposes a 20% accuracy-related penalty on any underpayment due to negligence, which specifically includes “any failure by the taxpayer to keep adequate books and records, or to substantiate items properly.” That’s 20% on top of the taxes owed, plus interest.

But it gets worse. Section 7203 makes willful failure to keep records a criminal offense. The penalties are up to $25,000 for individuals or $100,000 for corporations, plus up to a year in prison. While Wells notes that your typical shoebox client probably won’t face jail time, the existence of criminal penalties shows how seriously the IRS takes recordkeeping requirements.

The three warning signs every practitioner must recognize

These requirements create ethical obligations for practitioners too. Circular 230, Section 10.34(d) allows you to rely on client information, but requires “reasonable inquiries if the information as furnished appears to be incorrect, inconsistent with an important fact or another factual assumption, or incomplete.”

Wells calls these the “three I’s” that should trigger immediate concern. He shares a common example: “When I ask them what their business mileage is, they’ll just tell me a flat number that has three or four zeros at the end of it. As soon as I see that information, I already know, just in my gut looking at that information, whether it appears to be incorrect, inconsistent, or incomplete.”

When you spot these red flags, you can’t just ignore them. Wells describes the uncomfortable conversation that follows when he asks for a mileage log. “Nine times out of ten, they’re going to tell me they didn’t actually keep up with one.” At that point, you face a tough choice. Do you push harder for documentation, accept questionable information, or potentially end the client relationship?

“It might be a tough decision to stop working with a taxpayer because they want to claim a certain amount of miles,” Wells acknowledges. But when clients repeatedly ignore recordkeeping requirements despite annual reminders, “at that point, we might have to reconsider the relationship.”

How good records flip the script on IRS audits

While penalties provide the stick, there’s also a powerful carrot for maintaining proper records. Wells reveals how good recordkeeping can completely change the dynamics of an IRS dispute.

Normally, the IRS holds all the cards. The Supreme Court established in Welch v. Helvering (1933) that “the commissioner’s determinations have a presumption of correctness while the taxpayer bears the burden of proving the IRS position wrong.” Wells calls this “a tough hill to climb, especially for a taxpayer that has not kept good books and records.”

But IRC Section 7491 flips this burden. When taxpayers introduce credible evidence, comply with substantiation requirements, and maintain proper records, the burden shifts to the IRS to prove the taxpayer wrong.

“If a taxpayer shows up to an examination or an audit with good books and records,” Wells explains, “then the auditor knows that under Section 7491, now it’s on the IRS to prove the taxpayer is wrong.”

This creates “a more positive settlement climate,” according to a 2003 Tax Notes article Wells cites. Auditors become more willing to negotiate reasonable settlements rather than risk losing in court. He notes that even when a taxpayer takes a “technically incorrect position,” having good records to explain their reasoning can lead to much better outcomes.

Why the Cohan Rule won’t save your clients

Many practitioners rely on the Cohan Rule as a safety net, but Wells warns it’s been dangerously misunderstood. This 1930 court decision allows taxpayers to deduct “a reasonable estimate of the amount of a verifiable trade or business expense if the exact figure is unavailable.”

“I’ve heard, between bad tax advice on social media and some practitioners who haven’t really read the court case,” Wells says, people claiming “if the client doesn’t know how much, we’ll just fill in a number and appeal to the Cohan rule.” But that’s not how it works.

Courts take a harsh view of taxpayers trying to use Cohan without basis. In Barrios v. Commissioner (2023), the court stated it “bears heavily against the taxpayer who failed to more precisely substantiate the expense.” Translation: courts will slash your estimates, sometimes to zero.

Wells cites Williams v. US (1957), where the court refused to “guess” at expenses, calling relief without evidence “unguided largesse.” The message is clear: you need some reasonable basis for any estimate, not just a number that feels right.

Making matters worse, Section 274 completely blocks the Cohan Rule for certain expenses:

  • Travel
  • Entertainment
  • Business gifts
  • Listed property (especially vehicles)

For these categories, taxpayers must keep contemporaneous logs showing time, place, amount, and business purpose. Wells emphasizes how strict this is: “There have been tax court and federal court cases where the mileage log was simply thrown out and no deductions were allowed because the taxpayer attempted to recreate that log after the fact.”

Turn recordkeeping problems into profitable services

Instead of fighting poor recordkeeping every tax season, Wells outlines specific services that transform this challenge into recurring revenue.

His foundation is a “bookkeeping review service.” You’re not doing actual bookkeeping. Instead, you review the client’s records quarterly and flag issues. “We’re probably not going to look through a lot of five, ten, twenty dollar office expenses,” Wells explains. “But we might look through some expenses that are four or five, six figures.”

During these reviews, you might spot expenses that should be capitalized instead of deducted, deposits miscategorized as revenue when they’re actually loans, or aging receivables signaling cash flow problems. The key is efficiency. “They don’t take nearly as much time as actual bookkeeping does,” Wells points out.

He also strongly advocates for direct communication with clients’ bookkeepers, eliminating the game of telephone that wastes everyone’s time. Set up quarterly check-ins to discuss categorization questions, journal entries, and ownership changes before they become tax-time emergencies.

“This should not be free,” Wells stresses. “This should not be just included. You should not just start doing this out of the goodness of your heart.” Whether bundled into tax prep fees or structured as a monthly subscription, these services must generate revenue.

Some practitioners take this even further with preferred partner networks. Wells knows firm owners who refuse to prepare returns unless the books come from their vetted bookkeepers. While it sounds extreme, the benefits are clear. “They’re never going to have to worry about whether a deposit was really revenue or contribution of equity or new line of credit, because they trust the bookkeeper to have taken care of that already.”

For maximum scalability, Wells suggests creating educational resources. Use screen recording tools to solve common problems once, then share those videos with multiple clients. “Each time a client asks you a question, you know others have that same question,” he notes. This transforms repetitive education from a time drain into a reusable asset.

Listen to transform your practice

Recordkeeping isn’t optional; it’s legally required, with penalties ranging from 20% of underpaid taxes to potential criminal charges. But understanding this framework doesn’t just protect you and your clients from disasters. It opens doors to shift audit dynamics in your favor, negotiate better settlements, and create profitable advisory services.

Will you keep wrestling with shoeboxes every tax season, hoping estimates will pass muster? Or build systematic solutions that generate recurring revenue while protecting everyone involved?

Listen to the full episode to learn exactly how to implement these strategies in your practice. Because when you understand the legal framework—the requirements, the penalties, and most importantly, the opportunities—you stop just surviving busy season and start building a practice that thrives year-round.

Tax Law Rewards Professional Stagnation While Punishing Growth

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A Tennessee accountant diligently studies for and passes the CPA exam. His day-to-day work remains virtually identical: same clients, same responsibilities, same desk. Yet when tax season arrives, those CPA exam costs aren’t deductible. Why? Because becoming a CPA qualified him for a “new trade or business,” even though he had no intention of changing careers, and his actual work didn’t change at all.

This real case from Glenn v. Commissioner perfectly captures the absurd reality facing today’s professionals: the very credentials and education that make you more valuable in your current role often become non-deductible under tax law. Jeremy Wells dissects this paradox in his latest Tax in Action podcast episode, where he reveals how our tax system has created a knowledge economy trap that punishes professional advancement.

While tax law theoretically supports professional development through education deductions, it systematically penalizes advanced degrees, professional certifications, and career-expanding skills by classifying them as “personal investments” rather than business necessities. This leaves tax professionals and their clients caught in a regulatory maze where maintaining your current skill level is rewarded, while pursuing excellence faces potential penalties.

The Knowledge Economy Reality Check

“For quite a while now, most of the U.S. economy has been based on not the ability of people to produce things or do things with their hands, but rather the value of what they’re able to accomplish with their minds,” Wells explains.

The financial sector, insurance industry, and professional services all depend on knowledge work. Yet our tax system treats developing those valuable mental capabilities as personal indulgence rather than business necessity.

The existing education tax breaks demonstrate this disconnect clearly. The 529 plans that parents use to save for college offer no federal tax deduction for contributions, though some states do allow deductions. Student loan interest deductions under IRC Section 221 phase out based on income, effectively penalizing successful professionals. Education credits like the American Opportunity Credit and Lifetime Learning Credit focus on traditional college expenses, not the specialized training that drives value in today’s economy.

As Wells notes, these benefits can be rather limited. The problem isn’t that tax law ignores education entirely. It’s that the benefits don’t match the reality of professional development needs.

This brings us to the question Wells hears constantly from business owners: “Can I pay for my own education and use my business to do that?” The answer reveals just how complex this landscape has become.

Educational Assistance Programs: Promise and Pitfalls

The IRC Section 127 educational assistance programs initially appear to offer hope. These programs allow employers to provide up to $5,250 annually in tax-free educational benefits, and the definition of qualifying education is surprisingly broad.

Wells explains that under these programs, “education includes any form of instruction or training that improves or develops the capabilities of an individual.” Even better, “education is not limited to courses that are job-related or part of a degree program.” This could potentially cover everything from technical training to wellness courses that make employees “better people, more productive, happier.”

The program can cover tuition and fees, books, supplies, and equipment, and even student loan repayments. The definition of “employee” is also broad, including “self-employed individuals or what we might refer to as independent contractors.”

But here’s where the system reveals its bias against small business owners.

The fatal flaw lies in the anti-discrimination rules. Any business owner with more than a 5% stake in their company cannot claim more than 5% of the total benefits paid out by the program. As Wells explains, “If you are self-employed, and you want to use this program for yourself, and you have other employees, you, as a more than 5% owner of that business, cannot claim more than 5% of the benefits paid out by that program.”

The math is brutal. If you want to claim the full $5,250 benefit for your own education, your business would need to pay out at least $105,000 in total educational benefits to all participants. For most small businesses, this makes the program impractical.

The discrimination rules add another layer of complexity. Programs cannot favor highly compensated employees: those earning over $160,000 in 2025, those with 5% or greater ownership stakes, or those in the top 20% of employees ranked by compensation.

Wells notes that for many small business owners, this means they either “don’t do this program at all” or “just exclude themselves from the program.” And there’s another catch. Unlike cafeteria plans under IRC Section 125, you can’t offer employees a choice between the education benefit and additional cash compensation.

The program also has strict substantiation requirements. Employees must provide documented proof that expenses qualify, and they can’t double-dip by receiving reimbursement and then claiming education credits on their personal returns. Wells warns this is particularly important because “it’s entirely possible that that employee would then turn around and report those educational costs on their tax return and claim an education credit.”

When Business Owners Go Direct: The Section 162 Minefield

When educational assistance programs fail small business owners, they turn to direct business deductions under IRC Section 162. This is where things get really tricky.

Treasury Regulation 1.162-5 allows education deductions if the education “maintains or improves required skills” or “meets legal or employment requirements to maintain his or her present salary, status or job.” This generally includes professional continuing education and refresher courses.

The regulation also covers education to meet an employer’s minimum requirements “if the requirements are imposed for a bona fide business purpose.” Wells gives the example of requiring employees to take spreadsheet training because “we use a lot of spreadsheets in my business, and my employees need to be able to effectively use those spreadsheets.”

Even travel for education can be deductible if “the travel is directly related to the duties of the individual in employment” and “the major portion of that business needs to include activities directly maintaining or improving required skills.” However, taxpayers must allocate personal activities during the trip separately.

But here’s where the Tax Court draws its line in the sand.

The Tax Court’s War on Professional Growth

Treasury Regulation 1.162-5(b) establishes two types of education that are explicitly non-deductible, and the Tax Court has interpreted these restrictions aggressively.

First, taxpayers cannot deduct education that meets “necessary minimum educational requirements.”  Second, and far more damaging, education that “will lead to qualifying an individual for a new trade or business” is automatically disqualified.

The logic, Wells explains, is that these expenses are “essentially personal or perhaps capital expenditures” where “you’re investing in yourself.” The Tax Court views this as an “inseparable aggregate of personal and capital expenditures” rather than ordinary business expenses.

The cases reveal a pattern of hostility toward professional advancement that spans decades. In the Glenn case, the accountant couldn’t deduct CPA exam costs even though his work remained identical. The Tax Court ruled that becoming a CPA granted “certain rights, responsibilities, privileges that weren’t there before.”

The pattern repeats across professions. In Robinson v. Commissioner (1982), a licensed practical nurse completed an RN program while maintaining virtually identical duties. The Tax Court ruled against her because registered nurses have different capabilities than LPNs.

Even IRS employees get caught in this trap. In Weiler v. Commissioner (1970) and Taubman v. Commissioner (1973), IRS revenue agents couldn’t deduct law school costs despite arguing that legal training enhanced their current tax research abilities.

Law degrees face particularly harsh treatment. Wells notes that “law degrees generally qualify for a new trade or business” regardless of the taxpayer’s current profession or intentions.

The MBA Split Decision

The MBA cases show just how arbitrary these determinations can become. In 2016’s Gora v. Commissioner, the Tax Court allowed a financial controller’s executive MBA costs because his continued work in “management and finance” didn’t represent new qualifications.

Just one year later, in Kray v. Commissioner (2017), a computer design consultant’s identical executive MBA was ruled non-deductible because it qualified her for “new tasks” like “financial analysis, managing a business, managing and overseeing a staff.”

Wells warns that “an MBA may or may not qualify” as deductible, making this area particularly risky for taxpayers.

The Practical Reality for Tax Professionals

This creates impossible situations for tax professionals advising clients. The Tax Court’s standard isn’t whether you actually change careers or even want different opportunities. As Wells emphasizes, the keyword is “potentially”—education that could potentially qualify you for different work is probably non-deductible.

The system forces taxpayers to choose between pursuing valuable education that enhances their business capabilities but facing potential audit challenges, or limiting themselves to narrow, maintenance-level training that clearly fits within existing job requirements.

Wells notes that taxpayers must be “established in a trade or business” before education expenses become deductible, and the Tax Court has ruled that “a relatively short or temporary tenure in a job before starting the education doesn’t establish the taxpayer in the trade or business.”

Even holding a position doesn’t guarantee you’ve met minimum educational requirements. University teaching assistants, for example, haven’t met the minimum requirements for permanent faculty positions until they actually have their PhD.

Navigating the Knowledge Economy Trap

Our tax system rewards professional stagnation while punishing the learning that drives economic value. Tax professionals’ continuing education to maintain existing credentials? Fully deductible. Are the same professionals pursuing advanced degrees to better serve clients? Potentially non-deductible because it might qualify them for “new” responsibilities.

For tax professionals, this creates compliance challenges and ethical questions. Do we advise clients toward valuable education that faces potential tax challenges, or recommend they limit learning to “safe” options that maintain the status quo?

Wells warns that employers and self-employed individuals “really need to be careful when they’re trying to deduct those work-related education costs.” The Tax Court “can be pretty strict about education either meeting those minimum requirements for a profession or even more often than that, qualifying the recipient of that education for a new trade or business.”

Understanding these limitations is about recognizing how tax policy shapes professional development decisions across the entire economy. The knowledge economy demands continuous adaptation and skill development, but our tax code remains anchored to an industrial mindset that views capability expansion as personal indulgence rather than business necessity.

Listen to the full episode of the Tax in Action podcast for Wells’ complete analysis and detailed guidance to help clients make informed decisions about their professional development investments. Don’t let the knowledge economy trap catch you or your clients unprepared.

The Lookback Period Mistake That Turns Valid Refunds Into Permanent Losses

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Lenora Hamilton thought she had everything figured out. She filed her 2017 tax return in November 2021—late, but still claiming a $2,070 refund she believed was rightfully hers. The IRS immediately rejected her claim. She appealed, lost, and spent nearly a year fighting in federal court.

The final verdict in early 2025 delivered a crushing blow: the court ruled her claim was “timely filed,” but she couldn’t recover a single dollar. Not because the refund was wrong, but because she missed something called the “lookback period.” A technical timing rule had permanently erased her entire refund.

In a recent episode of the Tax in Action podcast, host Jeremy Wells used Hamilton’s story to explain the refund statute of limitations—a subject most tax professionals think they understand but actually don’t. The stakes are enormous: once these deadlines pass, Wells warns, “there’s virtually no going back.”

The Two-Step Framework That Trips Up Even Experienced Practitioners

Most tax professionals think the refund statute of limitations is straightforward. File within three years, get your refund. But Wells explains it’s a complex two-step process where each step has different rules and different consequences.

Step One: Can You File at All?

The first step determines whether you can file a refund claim. This “limitation period” is the later of either three years after the return was filed or two years after the tax was paid if no return was filed. Wells calls this the “refund statute end date,” and it’s your final deadline to file any claim.

Here’s the key detail that trips up practitioners: “The filing of an original return, not an amended return, begins the period of limitation,” Wells explains. This means if you amend a return filed years ago, you’re still working within the timeline set by that original filing date.

Step Two: How Much Can You Actually Get?

Even if you file a timely claim, step two determines how much you can recover through the “lookback period.” The rules change dramatically based on when you file:

  • File within three years: You can look back at the full three years
  • File after three years: Your lookback period shrinks to just two years

This is where Hamilton got trapped. The court found she filed a timely claim, satisfying step one. But because she filed her 2017 return so late—November 2021—her lookback period couldn’t reach back to her 2017 tax payments, which were deemed made on April 15, 2018.

As Wells puts it, “The court said she filed a timely claim for refund. However, for that timely claim, there was no refund available. What does that mean? How can that be?” To understand the answer, you have to know when the IRS considers payments “made” under tax law.

The Payment Timing Trap That Caught COVID-Era Taxpayers

The lookback period depends on when payments are “deemed made,” not when they actually happened. This creates counterintuitive situations that can permanently cost taxpayers money.

The Withholding Rule

Under IRC section 6513, all tax withheld from your paychecks during the year is deemed paid on April 15th of the following year. It doesn’t matter if the money was withheld in January or December—it’s all considered paid on April 15th.

For Hamilton, “Her 2018 withholding is deemed paid on April 15th, 2019, which is the 15th day of the fourth month following the close of that tax year.”

The COVID-19 Disaster

These timing rules created a perfect storm during the pandemic. The IRS postponed filing deadlines—2019 returns were due on July 15, 2020, and 2020 returns were due on May 17, 2021. But payments were still deemed made on April 15th of each year.

This trapped taxpayers who filed during the postponement periods. Someone who filed their 2019 return on July 15, 2020 (perfectly timely) might wait until July 15, 2023, to file a refund claim. Their three-year lookback would run from July 15, 202,3 back to July 15, 2020. But their 2019 payments were deemed made on April 15, 2020, which falls outside their lookback window.

Wells explains: “This left taxpayers who didn’t file extensions for those tax years stuck with potentially valid refund claims, yet they didn’t have any periods within the lookback period because those payments were still deemed filed as of April 15th.”

The IRS eventually provided relief through Notice 2021-21, but only after recognizing that its own timing rules created harsh consequences for taxpayers who did nothing wrong.

The Dangerous “Due Date” Myth Costing Taxpayers Money

A destructive misconception in refund statute law sounds perfectly reasonable: “You have three years from the due date to claim a refund.” 

But Wells makes it crystal clear that this perception isn’t accurate. “The end date is actually three years from the filing date or possibly two years from the payment date.” The due date might coincide with these periods for taxpayers who file on time, but it’s not what controls the deadline.

Why the Due Date Myth Fails

The due date myth crumbles in the exact situations where practitioners need precision most:

  • Late-filed returns: A taxpayer who files their 2020 return in September 2023 doesn’t have until April 15, 2024 to claim refunds. Their three-year period starts from September 2023.
  • Amended returns with post-deadline payments: Wells explains these create situations where “a valid refund claim made more than three years after the due date, could look back into those payments made after the deadline.”

The Hamilton case perfectly illustrates this. If you applied the due date myth, you’d think she was too late filing in November 2021 for a 2017 return. But the court found her claim was timely because the real rules don’t work that way.

The Professional Liability Risk

For tax professionals, relying on the due date myth creates serious liability exposure. When practitioners give advice based on this oversimplified rule, they risk costing clients money they can never recover.

Wells emphasizes the finality built into these rules: “Once that statute of limitations is up, once you have passed that refund statute end date, there is no going back with some very, very limited exceptions.”

Why These Rules Are So Unforgiving

The refund statute of limitations operates with mechanical precision, regardless of hardship or apparent unfairness. Courts consistently rule that these deadlines are clear and unambiguous, so there’s no room for equitable exceptions or reasonable cause relief.

The Finality Principle

Congress built finality into the tax code intentionally. As Wells explains: “There’s an implicit concept in the tax code that Congress has written into it. I tend to call it finality.” At some point, taxpayers should feel confident that old tax years are truly closed.

But this finality only works if practitioners understand the real rules. The Hamilton case, with its modest $2,070 refund that became a years-long legal battle, shows how even small amounts trigger the same unforgiving rules that govern million-dollar refunds.

The Stakes for Tax Professionals

These rules affect every practitioner who works with amended returns, late filers, or clients with potential refund claims. Understanding when the IRS deems payments made, how postponements interact with lookback periods, and when the due date myth doesn’t apply isn’t just technical knowledge—it’s client protection. And it can be the difference between recovering thousands of dollars and losing them forever.

When Time Runs Out, Money Disappears Forever

The refund statute of limitations represents tax law at its most technically demanding and unforgiving. The two-step framework of limitation periods and lookback periods creates a system where understanding timing rules can mean the difference between financial recovery and permanent loss.

For tax professionals, these rules represent the intersection of expertise and fiduciary responsibility. Relying on oversimplified rules or misunderstand the distinction between filing dates and due dates means risking giving advice that permanently costs clients money.

This finality places enormous responsibility on practitioners to understand and navigate these rules correctly.

Don’t let technical complexity cost your clients money they can never recover. Listen to Wells’ complete Tax in Action episode to master these critical timing rules and protect your clients’ interests and your professional reputation.