In the late twentieth and early twenty-first centuries, international adoption has become an increasingly visible and normative way to make a family. This chapter provides an overview of the histories of international adoption and the controversies surrounding it. It argues for the importance of artistic expression by adult international adoptees for a more comprehensive understanding of international adoption and its relationship to cultural security and insecurity. The chapter features the work of songwriter Jared Rehberg, painter Xhiv Bogart and writer Jane Jeong Trenka who were adopted from Vietnam, Guatemala and Korea, respectively. These artists reflect some of the breadth of adoptees’ national origins. They also utilize diverse genres to express, document and share their personal stories as well as collective histories of international adoptees. Cultural security for international adoptees can and should be strengthened when their needs for diverse and multiple forms of belonging are recognized and acknowledged.