This article discusses the dynamics of translation and exegesis documented in the body of Sanskrit-Old Javanese Śaiva and Buddhist technical literature of the tutur/tattva genre, composed in Java and Bali in the period from c. the ninth to the sixteenth century. The texts belonging to this genre, mainly preserved on palm-leaf manuscripts from Bali, are concerned with the reconfiguration of Indic metaphysics, philosophy, and soteriology along localized lines. Here we focus on the texts that are built in the form of Sanskrit verses provided with Old Javanese prose exegesis – each unit forming a »translation dyad«. The Old Javanese prose parts document cases of linguistic and cultural »localization« that could be regarded as broadly corresponding to the Western categories of translation, paraphrase, and commentary, but which often do not fit neatly into any one category. Having introduced the »vyākhyā-style« form of commentary through examples drawn from the early inscriptional and didactic literature in Old Javanese, we present key instances of »cultural translations« as attested in texts composed at different times and in different geographical and religio-cultural milieus, and describe their formal features. Our aim is to document how local agents (re-)interpreted, fractured, and restated the messages conveyed by the Sanskrit verses in the light of their contingent contexts, agendas, and prevalent exegetical practices. Our hypothesis is that local milieus of textual production underwent a progressive »drift« from the Indic-derived scholastic traditions that inspired – and entered into a conversation with – the earliest sources, composed in Central Java in the early medieval period, and progressively shifted towards a more embedded mode of production in East Java and Bali from the eleventh to the sixteenth century and beyond.