Focusing on the collective plot line of twenty Hebrew allegorical plays written in the Haskalah period, this study of the allegorical genre offers a new reading of a forgotten and understudied form of literary expression. The paper argues that in opposition to other literary genres that flourished during the first, idealist phase of the Haskalah period, the allegory took a persistently skeptical stance vis-à-vis the main ideological tenets of the Haskalah movement. Drawing on Walter Benjamin's view of the allegorical expression, and paying close attention to Hebrew allegory's role in forming the maskilic consciousness of history, I argue that while maskilic historical and meta-historical writings were clearly progressive and optimistic in their outlook on human agency in history, the Hebrew allegory presents historical reality as a doomed site of decay and corruption that is effectively controlled by malevolent agents. I argue that the famous (or notorious) redemption of historical time at the end of the allegories should not be read an expression of confidence in the metaphysical prowess of maskilic ideology. Opposing this common denigration of the allegory, my reading shows that far from being a mechanic or didactic genre, the allegory should be read as a rigorous disarticulation of central maskilic notions regarding the progressive view of history and nature, the role of human agency in history, and, more generally, the possibility of maskilic transformation of the world.