Song-dynasty Chan depended for its place in society and its financial resources on lay patrons. Educated gentleman-officials (shidafu) were the wealthiest and most powerful of men. From the time of Dahui Zonggao in the Southern Song, Linji teachers shifted from elaborate comments on gongan in periodic sermons to a new method of gongan inspection termed “critical phrase” (kan huatou). Scholars have argued that Dahui’s invention of huatou practice was primarily related to internal Chan rivalries for elite patrons. I argue that Dahui’s motive was also connected to a rivalry with Pure Land Buddhism over the making of appeals to lay followers among scholar-officials. Dahui was aware and tried to communicate the usefulness of huatou in addressing the elite laity’s doubts about birth and death, and in particular their anxieties about facing the decisive moment of death. Therefore, he developed a gongan discourse that is related to anticipation of dying by harnessing the power of doubt to create an experience of spiritual awakening.