This study uses stock repurchases announced by the Taiwanese listed companies as the subject to investigate the impact of psychological pitfalls on information senders' (repurchasing firm's managers) motivation and information receivers' (institutional and retail investors) behavioral reaction. The empirical results found that although stock repurchase announcements do not obviously change the behavior of information receivers, they demonstrate psychological pitfalls. Furthermore, in addition to the waiting for low stock prices for the distribution of free cash flow, gambler's fallacy may play an important role in the motivations of managers to make stock repurchase announcements. In the end, the influential factors of institutional investors' behavior are the perception of stock price rationality, perception regarding the possibility of distributing cash to shareholders, repurchase frequencies and insider buying, and the behavior of retail investors is influenced by insider selling.