Tax Implications of Remote Work

Apr 9, 2025

by Adam H. Thayer, Esq

The landscape of work has dramatically shifted since 2020, with remote work becoming a permanent fixture for many businesses operating across Rhode Island, Massachusetts and Connecticut. This transformation has created intricate tax implications that businesses must carefully navigate. Many are still grappling with the complex web of tax obligations that emerge when employees work remotely across state lines.

Understanding State Tax Nexus in the Remote Work Era

State tax nexus – the connection between a business and a state that triggers tax obligations – has become increasingly complicated with remote work. Traditionally, physical presence was the primary determinant of nexus. Now, having employees working remotely in different states can create nexus, potentially subjecting businesses to additional state tax obligations. For instance, a Rhode Island-based company with remote workers in Massachusetts and Connecticut may need to comply with tax regulations in all three states.

Withholding Requirements and “Convenience of Employer” Rules

Each state in the New England region handles withholding requirements differently for remote workers. Massachusetts previously maintained special COVID-19 withholding rules, which have since expired, returning to traditional sourcing rules. Connecticut follows the “convenience of employer” rule, which means that if an employee works remotely by choice rather than employer necessity, their income may be taxable in the employer’s state. Rhode Island, however, generally sources income based on where the work is physically performed.

Corporate Income Tax Considerations

Remote work can affect where businesses must apportion their income for tax purposes. Each state in our region uses different apportionment formulas, and the presence of remote workers can impact these calculations. For example, the Massachusetts Department of Revenue considers payroll factors in its apportionment formula, which may be affected by remote worker locations.

Sales Tax Obligations and Economic Nexus

Remote work arrangements can trigger sales tax obligations in multiple states. Since the Supreme Court’s decision in South Dakota v. Wayfair (2018), states have implemented economic nexus thresholds based on sales volume or transaction numbers. Businesses must monitor these thresholds carefully, as remote workers in different states might create additional sales tax registration and collection requirements.

Practical Solutions and Compliance Strategies

To manage these complexities, businesses should implement robust systems to track remote worker locations and time spent working in each state. Regular reviews of state tax obligations and thresholds are essential. Many businesses find success in using specialized software to manage multi-state tax compliance and working with tax professionals who understand the nuances of tri-state taxation.

Legislative Developments

State legislatures continue to adapt their tax codes to address remote work realities. The Multi-State Worker Tax Fairness Act, while not yet passed by Congress, could standardize state income tax treatment for remote workers. Businesses operating in our tri-state region should monitor these developments closely, as they could significantly impact future tax obligations.

Recommendations for Local Businesses

Companies should develop clear remote work policies that address tax implications, maintain detailed records of employee work locations, and regularly consult with tax professionals to ensure compliance. Consider implementing written agreements with remote workers that specify primary work locations and requirements for reporting any changes in work location. 

As the tax implications of remote work continue to evolve, businesses must stay informed about their obligations while maintaining flexible policies that accommodate both operational needs and tax compliance requirements. Regular review of tax positions and proactive planning can help minimize exposure and ensure compliance across state lines.

Contact Sayer, Regan & Thayer for more information on this topic.

Note: This article is for informational purposes only and does not constitute legal advice. Companies should consult with qualified legal counsel for specific guidance on regulatory compliance.