Firms can issue stocks classified in many ways, including in terms of voting rights, dividend rights, redemption rights, and conversion rights. This study investigates the desirability of giving firms greater freedom to choose their share classes. Using the 2011 Commercial Act amendment that significantly relaxed regulation over share classes in Korea, we study the motivation behind and effect of adopting two newly emergent classes: preferred stocks convertible to voting stocks at the discretion of management and preferred stocks redeemable at the discretion of investors. We find that firms adopt the former for managerial entrenchment purposes and destroy firm value by doing so, while firms adopt the latter in times of financial distress but fail to arrest the decline in firm value by doing so.