This article examines a series of messages concerning politics and geography that the religious order of the Vallombrosans embedded within a series of exorcism manuscripts and addressed to Lorenzo de’ Medici in the late fifteenth century. The Vallombrosans crafted their manuscripts to negotiate a host of troubles: schism over reform, friction with Lorenzo, diminishing social status, increased marginality, competition with rival religious orders, new definitions of orthodoxy, and alternate forms of religious devotion. I frame Vallombrosan troubles and their turn to exorcism as symptomatic of the increased predominance of Mendicant Observants over older orders, and link this shift to a newly active and politicized demonology.