Taxpayers sometimes engage in complex transactions with uncertain tax treatment, such as mergers, acquisitions, demergers and spin-offs. With the rise of global value chains and proliferation of multinational corporations, these transactions increasingly involve transnational financial arrangements and cross-border dealings, making tax treatment even more uncertain. If improperly structured, such transactions could have costly tax consequences. One approach to dealing with this uncertainty is to create a private rulings regime, whereby a taxpayer applies for a private ruling by submitting a statement detailing the transaction (proposed or completed) to the tax authority. The tax authority interprets and applies the tax laws to the requesting taxpayer’s specific set of facts in a written private ruling. The private ruling offers taxpayers certainty as to how the tax authority views the transaction, and the tax treatment the taxpayer can expect based on the specific facts presented. Private rulings are a common feature of many tax systems around the world, and their main goal is to promote tax certainty and increase investor confidence in the tax system. This is especially important in a developing country like Uganda, whose tax laws are often amended and may not anticipate emerging transnational tax issues. Private rulings in Uganda may be applied for in writing prior to or after engaging in the transaction. The Tax Procedures Code Act (TPCA), which provides for private rulings, requires applicants to make a full and true disclosure of the transaction before a private ruling may be issued. This paper evaluates the Ugandan private rulings regime, offering a comparative perspective by highlighting similarities and contrasts between the Ugandan regime and that of other jurisdictions, including the United States, Australia, South Africa and Kenya.