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In February 2020, the Massachusetts Supreme Judicial Court, in Citrix Systems, Inc. v. Commissioner of Revenue ruled that the sale of cloud computing subscriptions was subject to state sales tax because it was a transfer of tangible personal property. This was the first time a state’s highest court decided on the taxability of cloud computing products. As the industry continues to grow at a rapid pace, states have struggled to determine how to tax it. Some states find these products to be a non-taxable service, whereas others stretch their definitions of tangible personal property to allow taxation. This Comment argues that states cannot continue to make courts improperly fit new technology into outdated law, as in Citrix Systems, Inc. States must instead take aggressive steps to amend their tax statutes to partake in the bountiful profit of cloud computing and other unavoidable innovations in technology to come.