This study examines the literary and jurisprudential dimensions of linguistic expressions in the process of legal interpretation, applying a semantic approach to the analysis. Key issues such as designation (wadh), signification (dalālah), and the differentiation between the intentional and practical will (irādah isti‘mālī vs. irādah jiddī) of the legal authority are explored. Given the diverse linguistic tendencies and textual markers involved in deriving meaning (madlūl)—alongside the impact of contextual background on comprehension—the study identifies common linguistic principles, authorial intent, and semantic objectivity as essential components within legal hermeneutics. The findings suggest that discussions of linguistic expressions in Usul al-Fiqh (principles of jurisprudence) rely heavily on textual reasoning, lexical clarity, and customary linguistic interpretations. These elements are crucial in determining the precise meanings of words, sentence constructions, and semantic features, all of which have wide applications in Islamic legal reasoning. The study emphasizes that the systematic treatment of linguistic expressions within jurisprudential methodology reflects the fundamental necessity for scholars in legal hermeneutics to apply semantic analysis in order to ensure an accurate understanding of a speaker’s intended meaning and to derive sound legal rulings. Employing a descriptive-analytical approach, this study explores case examples such as the derivation of legal principles (mushtaq) from Quranic verses and Hadith texts, offering insights into the semantic implications for contemporary jurisprudential matters—including usufruct rights (sarf al-milk), chess (shatranj), Bitcoin, and other cryptocurrencies. Furthermore, the study engages with linguistic debates surrounding designation (wadh), usage (isti‘māl), and word signification (dalālat al-alfāz)—issues that have either not been extensively examined in literary disciplines or remain insufficiently analyzed within jurisprudence. Ultimately, the research traces the process by which semantic manifestation (ẓuhūr al-ma‘nā) is refined and completed in legal reasoning.