Maryland’s digital advertising services tax, which was enacted in February 2021, has faced heavy opposition on several fronts. In October 2022, a Maryland state judge struck down the tax, concluding that it violated the Internet Tax Freedom Act, the Commerce Clause of the U.S. Constitution, and the First and Fourteenth Amendments of the U.S. Constitution. The Comptroller of Maryland appealed this decision, but on May 9, the Supreme Court of Maryland concluded that the Circuit Court lacked jurisdiction over the action because the appellees failed to exhaust their administrative remedies. The Maryland Supreme Court vacated the Circuit Court decision and remanded the case to the Circuit Court with directions to dismiss the action. As of April 30, Maryland had collected $107 million in digital advertising taxes from 74 taxpayers and had issued refunds of $14.5 million since the tax became effective in 2022. Maryland’s Department of Legislative Services had initially estimated that tax revenue in 2022 would be $250 million. The recent decision of the Maryland Supreme Court casts doubt on whether potential taxpayers can opt not to pay the tax, while preserving their right to pursue a refund in the event the tax is ultimately struck down. Taxpayers who have opted not to pay the tax may continue to refrain from paying and contest an assessment by the Maryland Comptroller’s Office, but they may be exposed to monetary and criminal penalties for failing to file required tax returns and paying the required taxes, including the timely payment of estimated taxes.