Interaction with illegitimate and oppressive rulers is one of the most important and complex issues of Imami political jurisprudence, especially during the era of occultation, because it has wide-ranging consequences for the individual and social lives of Shiites and requires a well-founded analysis. This article, with a descriptive and analytical approach, examines the jurisprudential foundations of “interacting with an oppressive ruler” from the perspective of Sahib Jawaher, based on jurisprudential texts, narrations of the Infallibles (AS), consensus of jurists, and rational arguments. The findings show that Sahib Jawaher considers the oppressive ruler to lack divine legitimacy and presents a threefold framework for interaction: absolute prohibition of cooperation in forbidden matters and aiding in oppression, permission with aversion in permissible matters, and the desirability of cooperation in order to protect the interests of believers and ward off greater corruption. In addition, the permissibility of cooperation in situations of coercion, the distinction between primary and defensive jihad, and the legitimacy of seizing government property such as zakat, tribute, and division have been emphasized. This coherent approach, while adhering to the fundamentals, offers practical strategies for managing individual and social life in the face of oppressive governments.