When Muslim conquests brought Islam as a new religion into the Byzantine Empire, the veracity of its claim to prophecy was immediately challenged by the established monotheistic faiths. Hadith scholars were the earliest contributors to Dala’il al-nubuwwa (signs of prophecy) literature, which sought to defend their Prophet from non-Muslim offense by providing indubitable evidence for his prophetic status from the vast body of hadith literature. During the intellectually formative 3rd/9th and 4th/10th centuries, Dala’il al-nubuwwa literature evolved at the nexus of inter-religious debates, the development of various Islamic intellectual fields, and religio-political as well as social movements within the rising Islamic empire. However, while these hadith compilations were squarely situated in the scholarly circles of muhaddithun and upheld their criteria of authenticity, such as isnad criticism, Western scholarship has almost completely neglected this type of hadith literature and associated it with the popular story tellers, instead. This paper will explore the strategies hadith scholars contributing to this literature employed in order to maintain the collective authority of the prophetic tradition while incorporating the intricacies of religious discourses that were prevalent at their time – both in inter-religious debates and among various fields of Muslim scholarship. Based on a close study of early hadith-based Dala’il al-nubuwwa compilations, such as Ma‘mar b. Rashid (d. 153/770), Ibn Sa‘d (d. 230/845), and the unique manuscript of al-Jazajani (d. 259/873), as well as prominent later compilations, such as Abu al-Nu'aym (d. 429/1038) and al-Bayhaqi (d. 458/1066), this paper will highlight the shifting thematic strands found in this literature and will argue for a consistently increasing awareness and conscious acknowledgment of theological debates among these hadith scholars. This paper will, therefore, emphasize that Dala’il al-Nubuwwa literature showcases the eventual subsiding of a strict division between the muhaddithun’s textual approach and the theologians’ speculative approach to presenting ‘proofs of prophecy’.