. This research examines the linguistic structure of the conditional sentence in early grammatical tradition, particularly in Kitab Sibawayh, tracing its methodological and practical impact on deducing suspended rulings (Al-Ahkam Al-Ta’liqiyyah) from the jurisprudential verses (Ayat Al-Ahkam) of the Qur’an. It aims to deconstruct Sibawayh’s philosophy of entailment (Al-Falsafah Al-Luzumiyyah) and his concept of suspension (Al-Ta’liq), to clarify the semantic differences between conditional particles and their role in guiding jurisprudential rulings, and to trace instances of deviation (Al-Inziyah) between the literal grammatical structure and the objectives of Sharia (Maqasid).

The research adopts a descriptive-analytical approach to examine Sibawayh’s statements, supported by a comparative approach in presenting the interpretations of jurists and commentators. The applied study covers acts of worship (the verse of ablution), transactions (the verse of debt), punishments (the verse of theft), and expiations (the verse of Zihar), and investigates particles such as the probabilistic (In) and the deterministic (Itha), the effect of the response particle (Faa), and implied and gradual conditional structures.

The study finds that Sibawayh’s concept of Al-Ta’liq represents an early foundation for textual coherence, and that differences between grammatical particles served as a jurisprudential standard for mujtahids in regulating the allowances and strict rules of Sharia. It also shows that grammar in Al-Kitab functioned as an interpretative safeguard against hasty literal readings, confirming a complementary relationship between grammar and jurisprudence. The study recommends rereading Sibawayh’s heritage through a purpose-oriented lens and establishing a specialized field, Usuli Grammar, integrating applied linguistics with Islamic legal theory.