This chapter explores the dental appearance, health risks, social roles, and procedures related to dental filings and inlays among the ancient Maya. To this end, skeletal data, portraiture, and ethnographic information from the Maya Lowlands were surveyed. The results show that the majority of adult dentitions had been modified during the first millennium AD, many of which emulated the Maya solar sign and sacred wind forces. The initial operation was usually performed in youngsters, although older age groups were subject to the practice as well. Maintenance measures were taken in the form of additional filing and tooth extraction, especially once tooth wear and decay set in. During the heydays of Lowland Maya kingdoms, dental reductions and inlayed materials trace varied regional and local traditions. Past the Maya collapse, during the Postclassic period, tooth modifications turned into a standardized, mostly female practice that was accomplished exclusively by dental filing.