Elections in the wake of dramatic transitions from authoritarian regimes to democracy may confront voters with choices that are unattractive or bewildering, or both. This chapter examines the conditions that produce tractable sets of party options for voters, presents cross-national data on the choice sets and competitiveness in elections after dramatic transitions, and examines how the electoral formula used in proportional elections can affect electoral outcomes. The chapter argues that, in transitional contexts characterized by high uncertainty, electoral rules that reward economies of moderate scale, such as the Hare quota formula, can encourage the development of attractive choice sets. As democracies and party systems develop, however, the case for electoral rules that confer representational bonuses on winning parties gains traction.