Can a constitution born in dictatorship serve democracy, or is it inevitably tainted by the circumstances of its birth? This question is central in Chilean politics today, but Chile is not alone. Roughly 20 percent of constitutions in force today were drafted during undemocratic periods. Chile’s constitution, however, is part of a smaller set which we call transformational authoritarian constitutions. These constitutions (1) are explicitly framed as helping to structure a return to electoral democracy after a period of time; (2) reflect certain policy goals designed to be permanent; and (3) contain an enforcement mechanism to ensure that both these goals are met. The chapter then goes on to consider how constitutional reform should be achieved, drawing on comparative evidence.