[17][18][19] Despite Sibawayh's renowned scholarship, his status as a non-native speaker of the language is a central feature in the many anecdotes included in the biographies.

The accounts throw useful light on early contemporary debates which influenced the formulation of the fundamental principles of Arabic grammar.

In a story from the debate held by the Abbasid vizier Yahya ibn Khalid of Baghdad on standard Arabic usage, Sibawayh, representing the Basra school of grammar, and al-Kisa'i, one of the canonical Quran readers and the leading figure in the rival school of Kufa,[20] had a dispute on the following point of grammar, which later became known as المسألة الزنبورية al-Mas’alah al-Zunbūrīyah ("The Question of the Hornet").

Sibawayh proposed finishing it with fa-'iḏā huwa hiya (فإذا هو هي), literally "and-thus he [is] she",[22] using "he" for the scorpion (a masculine noun in Arabic) and "she" for "stinging, bite" (a feminine noun), arguing that Arabic does not need or use any verb-form like is in the present tense, and that object forms like ('iyyā-)hā are never the main part of a predicate.

Al-Kisa'i argued instead for fa-'iḏā huwa 'iyyā-hā (فإذا هو إياها), literally "and-thus he [does] onto-her", supporting the object pronoun -hā ("her") with the particle 'iyyā-.

When the student revealed who he was and what had happened, al-Kisa'i approached the Caliph Harun al-Rashid and requested punishment from him knowing he had had a share in "killing Sibawayh.

Both Sibawayh and his teacher al-Farahidi are historically the earliest and most significant figures in respect to the formal recording of the Arabic language.

Sibawayh's book came from flourishing literary, philological and tafsir (Quranic exegetical) tradition that centred in the schools of Basra, Kufa and later at the Abbasid caliphal seat of Baghdad.

[13] Al-Mubarrad is quoted as posing the question to anyone preparing to read the Book, Al-Mabriman of al-'Askar Mukram and Abu Hashim debated educational approaches to the exposition of Al-Kitāb.

Ibn Durustuyah an associate and pupil of al-Mubarrad and Tha'lab wrote The Triumph of Sibawayh over All the Grammarians, comprising a number of sections but left unfinished.

[13] Al-Kitāb, comprising 5 volumes, is a long and highly analytic and comprehensive treatment of grammar and remains largely untranslated into English.

Due to its great unwieldiness and complexity the later grammarians produced concise grammars in a simple descriptive format suitable for general readership and educational purposes.

Abu Hayyan al-Gharnati, the most eminent grammarian of his era, memorized the entire Al-Kitāb, and equated its value to grammar as that of hadiths to Islamic law.