We first discuss a more nuanced view of the tax compliance game from the evolving perspective of behavioral economics. This discussion is followed by a more traditional analysis of issues related to taxation of the small drawing on recent insights and policy interventions. Our discussion generally blends issues of tax structure with various facets of tax administration and enforcement. In most instances the tax instrument in question is the VAT since it is the dominant revenue source in most developing countries, though we recognize there are compliance problems with all revenue instruments.