This paper brings into discussion and comparison two texts of monastic regulations (Mong. ǰayiɣ): a short document composed by the Thirteenth Dalai Lama in 1906 during his visit to Mongolia and on the occasion of his visit to Gandantsenpilling monastery, and a text of rules and regulations for Mongolian monastics, entitled Rules for the Monasteries of Mongolia (Tib. Sog yul kyi dgon sde rnams kyi bca’ khrims), composed by the Fourteenth Dalai Lama in August 2006. A comparison between these two documents sheds some light on the concerns and conditions of monastic life in Mongolia during two different periods—the Bogd Khaan autonomous Mongolian state, established in 1911 after the fall of the Qing dynasty, and the early period of the revitalization of Buddhism in Mongolia after seven decades of communist suppression of religion. Analysis of these two documents also illustrates the ways in which the two Dalai Lamas understood the conditions of Mongolian Buddhist monasticism during their visits and the types of regulations that needed to be instituted for Mongolian monasteries of their times. It also illuminates the intersection of transregional Géluk monastic education and the religious and political authorities.