As the governments of countries in Eastern Europe and the former Soviet Union continue to grapple with the challenges of transition, many significant policy developments have already taken place over the past six years, developments of interest to policymakers and economists alike. Conditions in these Countries in Transition (CITs) have presented a formidable challenge to reformers, a challenge that has been met with bold, rapid action in some cases; timid, tepid response in others. Now, as CITs enter the seventh year of transition, perhaps lessons can be drawn from their experience which may be of value in the future to those countries that will, in time, be in transition from socialist to market-based economic systems. The goal of this paper is to review the transition experience in tax reform over the past six years, offer a preliminary evaluation of the impact of different approaches to tax reform, and extract lessons from the successes and failures of this experience. The rest of the paper is organized as follows. We start with a brief review of tax systems in socialist planned economies in Section 2, and then move on to an examination of the enduring legacy of tax systems under central planning in Section 3. Many of the failures, problems, and idiosyncrasies of the reform efforts during the transition can be traced to the past, when these tax systems started. In Section 4, we review the two general paradigms for reform that policymakers faced early on in the transition: the adoption wholesale of a western-type, modern tax system or a tax system adapted to transition economies. Many of the current problems in the fiscal arena can be partially attributed to the scope, pace, and stability of the reform process. In Section 5 we offer a short description of the evaluation and current structure of tax systems in CITs. In Section 6 we make a preliminary attempt to quantify the impact of different approaches to tax reform on economic performance of CITs. In Section 7, we summarize the lessons from tax reform in CITs. While no strategy could be comprehensive and infallible, there are lessons to extract from the concrete experiences, relatively better practices and mistakes of CITs for the remaining centrally-planned economies when they in turn embark upon comprehensive market reform.