The advent of the digital economy has had profound implications for taxation. Jurisdictions have been forced to adapt their tax systems as they become increasingly unsuited to the realities of modern commerce. While Singapore has largely followed international developments, particularly in the area of international taxation, it has often made innovative policy decisions in line with its national interests. The various policy decisions that Singapore has made on taxing the digital economy span both international and domestic taxation. In the area of domestic tax, the policies have been further divided by subject matter, such as e-commerce, digital tokens, automation, and electronic instruments. Other jurisdictions will face similar choices when considering how to adapt their domestic tax systems for the digital economy, and the tax policy decisions made by a small, highly open economy such as Singapore may provide insights for such jurisdictions.