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. The Ugandan private rulings regime has a number of strengths. It is not just an administrative measure as in some jurisdictions, but is based on statute. Rulings are issued from a central office – instead of different district offices, which may result in conflicting rulings. Rather than an elaborate appeals process, the private ruling is only binding on the URA and not on the taxpayer, so a dissatisfied taxpayer can simply ignore the ruling. The URA team that handles private rulings has diverse professional backgrounds, which allows for a better understanding of applications. There are, however, a number of limitations of the Ugandan private rulings system. The procedure of revocation of a private ruling is uncertain. Private rulings are not published, which makes them a form of ‘secret law’. There is no fee for private rulings, which contributes to a delay in the process of issuing one. There is understaffing in the unit that handles private rulings. Finally, there remains a very high risk of bias against the taxpayer because the unit is answerable to a Commissioner whose chief mandate is collection of revenue. A reform of the private rulings regime is therefore necessary, and this would include clarifying the circumstances under which revocation may occur, introducing an application fee, increasing the staffing of the unit responsible, and placing the unit under a Commissioner who does not have a collection mandate. While the private rulings regime in Uganda has shortcomings, it remains an essential tool in supporting investor confidence in the tax regime.