This paper follows one woman's pursuit of upasampadā (higher ordination) to examine how contemporary Theravāda women negotiate authority, lineage, and gendered restrictions across Thailand and Sri Lanka. Bhikkhuni DK's experience illustrates how ordination is shaped not only by the canonical scriptures of the Pāli Tipiṭaka but also by how women interpret and reenact these texts, within spaces of agency produced by competing monastic interpretations of the Gurudhammas. As the Thai Saṅgha does not currently permit Bhikkhunī ordination, Sri Lanka has become the place where Thai women travel to be ordained, allowing them to follow their spiritual needs and to identify and live as Bhikkhunī. Drawing on two years of ethnographic fieldwork, this study retraces Bhikkhuni DK's story, alongside many women before her, to show how gender inequality is grounded in canonical texts and sustained through institutional practices, while showing how practitioners challenge these inequalities in their everyday lives, reinterpreting the traditional view of Bhikkhunī ordination. The paper argues that Bhikkhuni DK's ordination journey exemplifies a transnational religious strategy in which doctrinal authority, institutional power, and embodied practice intersect. By tracing her movement between Thailand and Sri Lanka, it illustrates how contemporary Bhikkhunī ordination is produced through contested interpretations of Buddhist authority, transnational networks, and embodied commitment, experienced as both a spiritual aspiration and a prolonged process of mediation, endurance, and adaptation. The case contributes to broader debates on religious authority and gender in Theravāda Buddhism by demonstrating how women's ordination is not only a doctrinal question but also a lived process of negotiation and transformation.