We investigate a bargaining setting between an “informed” player, who has private information, and an “uninformed” player. The informed player has the option to truthfully disclose private information in two unique environments. In the first environment, the informed player is randomly matched with an uninformed player and, after matching, can voluntarily disclose private information prior to a negotiation taking place. In the second environment, the informed player can voluntarily disclose private information before any endogenous matching between players (and subsequent negotiation) takes place. We begin by examining these environments theoretically. When disclosure occurs after matching, we show that low informed types should disclose more often than high informed types to avoid disagreement. However, when disclosure occurs before matching, for a range of parameter values, we show that high informed types should disclose more than low informed types to secure a better match. We test these predictions in a controlled human-subjects experiment and verify many of the theoretical predictions. Among other results, we find that low informed types do indeed disclose their private information to avoid disagreement and that, when it is in their interest to do so, high informed types disclose their private information to secure a better match. Another key insight is that high uninformed types benefit from disclosure regardless of whether it occurs before or after matching. This paper was accepted by Axel Ockenfels, behavioral economics and decision analysis. Supplemental Material: The online appendix and data files are available at https://doi.org/10.1287/mnsc.2022.03566 .