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Challenges of Sales Tax for Small Businesses: Navigating Compliance

Barkin Doganay · October 23, 2023 · 4 min read

Challenges of Sales Tax for Small Businesses: Navigating Compliance

For small businesses, encountering significant tax troubles can be remarkably easy, particularly through inaccurate withholding and remittance of sales tax. While various factors contribute to this issue, once a business falls behind, rectifying the situation is often more daunting than addressing income tax matters.

Outlined below is a comprehensive exploration of why many small businesses grapple with sales tax challenges and how these obstacles can be mitigated. Additionally, strategies are discussed to prevent sales tax liabilities from jeopardizing the survival of your business.


In the Commonwealth of Massachusetts, retail sellers are mandated to collect a sales tax equivalent to 6.25% of the purchase value of goods from customers. The complexity of sales tax dilemmas typically arises from the fact that the liability is calculated based on gross sales, disregarding net profits after expenses. Unlike income tax liability, which is incurred only when business activities yield economic profits, sales tax liability can accumulate even in cases where businesses operate at a loss.

Legally, sales tax is the responsibility of the buyer. However, in Massachusetts and many other states, retail sellers are required to withhold sales tax at the point of sale and subsequently remit it to the government. Failure to properly withhold sales tax from customers may lead to the seller being held primarily liable. Consequently, inattentive sellers can inadvertently become accountable for taxes that should have been the responsibility of their clientele.

Beyond Goods: A Wider Scope

Conventionally, sales tax obligations arise from the retail sale of goods in the ordinary course of business. However, translating this straightforward concept into real-world situations can prove challenging. Consider scenarios where an invoice includes not only charges for goods but also additional fees for services such as installation, shipping, or technical support. The tax treatment of these supplementary line items varies from state to state and may even hinge on how invoices are structured.

Moreover, changing trends have broadened the definition of taxable sales over the past two decades, encompassing an array of transactions. Many states now impose taxes on various service transactions, including prepared meals, tanning bed use, haircuts, software downloads, and media streaming services. Notably, the meal tax can pose a substantial liability for restaurants based in Massachusetts.

Potential Severe Penalties

The possibility of sales tax liability reverting to the seller in the event of an error necessitates meticulous attention to compliance. Negligence or significant errors can lead to penalties of 20% or more. State revenue authorities, such as the Massachusetts Department of Revenue, may impose further aggravated penalties on sellers who collect sales tax from customers but fail to remit the collected amounts to the government. Businesses facing challenges might view the state's funds as a readily available source of liquidity, but such a short-term solution can become a long-term burden when hefty penalties and interest are later imposed on the borrowed amount.

Entities taxed as pass-throughs (e.g., LLCs or partnerships) for income tax purposes are considered primary taxpayers for sales tax obligations. However, this distinction often doesn't shield individuals actively engaged in business management.

In cases of significant underpayment of sales tax, states may pursue owners, managers, and staff with control over company assets on a personal level to recover unpaid tax and penalties. Multiple parties may be targeted simultaneously until the liability is settled. Consequently, individuals in financial management roles within noncompliant businesses should carefully evaluate their personal exposure in relation to the company's position.


Businesses with narrow operating margins are particularly susceptible to the severity of sales tax issues due to their reliance on gross sales for liability calculations. This is especially pertinent for Massachusetts-based restaurants that are obligated to collect and remit the meal tax.

Engaging professionals well-versed in sales tax reporting obligations can greatly assist in safeguarding small businesses. This often entails developing effective strategies to address noncompliance before an audit or crafting a well-structured audit response to minimize personal liability. If you suspect your business may be facing sales tax compliance issues, seeking professional guidance promptly is recommended.

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