This article offers a thorough overview of the U.S. withholding tax regime related to international payments. It discusses identifying payment types, determining payee status, applying relevant withholding rules, treaty relief, documentation and reporting requirements, and practical steps for compliance. The goal is to assist withholding agents and U.S. payors in fulfilling their obligations and minimizing the risk of penalties.

Canadian investors in U.S. LLCs face complex tax issues due to differing U.S. and Canadian classifications. While the U.S. treats LLCs as flow-through entities, Canada views them as corporations, often causing double taxation and heavy compliance burdens. Careful planning—such as using U.S. C-corporations or alternative structures—can help align tax treatment and reduce cross-border inefficiencies.

Overview of Non-Resident Withholding Tax on Canadian Dividends

On September 25, 2025, the Supreme Court of Pennsylvania affirmed a lower court decision declaring that Pittsburgh's “jock tax” does not comply with the Pennsylvania Constitution.

What kind of tax consequences will a Canadian resident athlete, like McKenna, who is scheduled to earn income from his name, image, and likeness (NIL) through advertising or other campaigns, face in both the United States and Canada?