This study analyzes and examines the contribution of stock repurchases to the value of the firm in different degrees of insider trading restrictions to see whether and how different insider trading environments affect the relation between stock repurchases and firm value. Since insider trading restrictions are not worldwide standardized, each country or region has its own regulations. By using an intertemporal sample from 21 developed or highly developing countries and regions, I find that stock repurchases contribute less to firm value in countries with weak insider trading restrictions than in countries with strong insider trading restrictions after controlling the proxy for the country level investor protection environment, gross domestic product per capita and gross domestic product growth. It contributes to the knowledge of influences of insider trading restrictions upon stock repurchase and firm value in a cross-country/region setting, providing some new insight on the role of insider trading to see whether or not it should be regulated to create a better market environment.