This dissertation studies how institutional design and market incentives shape behavior in environments with imperfect information and limited transfers. It examines two settings - professional certification and media markets - where rules governing information acquisition and transmission affect selection, political outcomes, and welfare. Combining theoretical models with empirical evidence, the dissertation shows how informational policies shape strategic behavior. The first chapter studies attempt limits in professional licensing exams. Using variation in Bar Exam policies across U.S. states, I document that jurisdictions with attempt limits have higher per-session pass rates among repeat candidates, while first-time pass rates remain largely unchanged. I rationalize this pattern with a dynamic principal-agent model in which candidates choose when to take the test and may improve over time. Attempt limits create endogenous test-taking costs that induce self-selection, improving screening but restricting future opportunities. I characterize when attempt limits are optimal and show that they are desirable when they successfully induce sorting. The second chapter extends this framework by allowing the principal to choose both the passing threshold and the information structure of the test. Optimal policy depends on which types the test identifies more effectively. When tests are better at detecting low-ability candidates, the principal relies on high difficulty with unlimited retakes. When tests are more informative about high-ability candidates, attempt limits with intermediate difficulty become optimal. Test design also depends on intertemporal incentives: when candidates and the principal are relatively impatient, the optimal test better detects low-ability candidates; otherwise, the principal prefers tests more informative about high-ability candidates. The third chapter studies media capture in local news markets. I develop a model in which a newspaper chooses reporting quality while facing potential political influence from an incumbent and balancing subscription and advertising revenues. The relationship between advertising revenues and media bias is generally non-monotonic: advertising may initially increase bias by lowering subscription prices, which makes worse reporting quality more tolerable to readers, but eventually reduces bias by raising the compensation required to sustain distortion.