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Restructuring transition enterprises has been slow. Many firms remain unprivatized and the new owners take inadequate measures. A structural barrier is identified at the government level: The government designs the privatization program which leads to restructuring. However, transition governments are in a fiscal squeeze because restructuring relocates costs from firms to the public budget. Nevertheless, the deficit should be kept within narrow limits. This problem is analyzed within a stylized dynamic model. It is found that the fiscal constraints can delay or halt privatization. Careful sequencing of policy and a low ratio of wage-to-profit taxes can remedy the problem.