The first essay examines how the outcome of prior repurchasing activity influences future repurchasing decisions. We find strong evidence that future decisions to repurchase equity are negatively influenced by poorly timed past repurchases. Specifically, we show that the past losses on stock repurchases reduce the propensity to engage in additional repurchases in the future. We find almost no evidence that past gains on repurchases positively or negatively influence future repurchasing activity. These results are robust to various firm characteristics, estimation and sampling methods. Further analyses show that losses on past repurchases influence dividend policy. We show that the dividend-repurchase substitution rate slows down for firms t...