Herman Melville’s "Bartleby, the Scrivener" has become a hit in American literature. The particular term "the Bartleby industry" indicates its importance and popularity in academic fields. The short story has been discussed regarding Marxism, autism, linguistics, legal systems, representation, and so on. All of these discussions revolve around Bartleby’s famous expression, "I prefer not to." Bartleby’s ambiguous expression evokes conflicting interpretations among scholars: "the will to nothingness" and "the nothingness of the will," that is, the active and negative resistance that Bartleby engaged in. Although there are so many ways to interpret Bartleby’s expression, none seriously focuses on the influence of technological devices in 19th-century America on the formation of Bartleby’s reaction to his external environment. This paper aims to reinterpret Bartleby’s enigmatic demeanor and the circumstances of his death to argue that both his expression and his death serve as a symbolic gesture of rupture, resisting the driving force of Melville’s contemporary technologically driven, industrialized society.