We study the role of incomplete information and outside options in determining bargaining postures and surplus division in repeated bargaining between a long‐run player and a sequence of short‐run players. The outside option is not only a disagreement point, but reveals information privately held by the long‐run player. In equilibrium, the uninformed short‐run players' offers do not always respond to changes in reputation and the informed long‐run player's payoffs are discontinuous. The long‐run player invokes inefficient random outside options repeatedly to build reputation to a level where the subsequent short‐run players succumb to his extraction of a larger payoff, but he also runs the risk of losing reputation and relinquishing bargaining power. We investigate equilibrium properties when the discount factor goes to 1 and when the informativeness of outside options diffuses. In both cases, bargaining outcomes become more inefficient and the limit reputation‐building probabilities are interior.