The inscriptions from Khirbet Beit Lei and Khirbet el-Q?m were originally situated in hewn burial caves in the southern Shephelah. Since their original publication in 1963 and 1970 respectively, new technologies have become available for photographing epigraphic material. Reflectance Transformation Imaging (RTI) is a technique that combines multiple light angles to facilitate enhanced views of the object. This dissertation uses new photographs as the basis for a fresh assessment of the cave inscriptions. Building upon previous paleographic and archaeological analyses of the inscriptions and their setting, this study presents an integrative analysis of the source and purposes of the inscriptions in context. Viewing the inscriptions as physical objects, the production and preservation of which involved numerous processes, each of which were socially and culturally informed, facilitates a more holistic treatment of the inscriptions. When the inscriptions are examined in the context of various classifications of inscribing, such as informal inscribing, ritual inscribing and mortuary inscribing, a number of themes emerge. The cave inscriptions represent commemorative inscribing, physically memorializing identities and events on the tomb walls. Overwriting and other repetitious inscribing illustrate the importance of the act of inscribing and hint at a ritual or performative use of writing. The unique combination of texts and images along with the burial setting and placement of the inscriptions betray an innovative use of both the content and the space. Given the context of conflict besetting the kingdom of Judah during much of the Iron Age IIB, there are multiple possibilities regarding the more specific impetus for the inscriptions. While it is not possible to ascertain whether or not the inscriptions were associated with the burial use of the tombs, this contextual study highlights the fact that the inscribers would have already been affiliated with the space and that they selected the tomb setting because the meaning of the space aligned with the purposes of the inscribing.