This study undertakes a systematic analysis, within the framework of ḥadīth scholarship, of reports attributing to Umayyad rulers the performance of ṣalāt outside its prescribed times during the period from the reign of Muʿāwiya b. Abī Sufyān to that of ʿUmar b. ʿAbd al-ʿAzīz. Issues previously explored in scholarly literature-such as whether the khuṭbas of Friday and Eid prayers were delivered prior to the ṣalāt, and whether a two-rakʿa supererogatory prayer was observed after the ʿaṣr prayer-have been excluded from the scope of this investigation. Likewise, the influence of these reports on the sects and their employment in contemporary polemics fall outside the limits of this study and are considered matters for separate research. The transmission of such reports with direct attribution to the Prophet, while disregarding their historical contexts and omitting expert assessment, has the potential to lead to significant historical misjudgements and unwarranted controversies. In this regard, it is of particular importance to first evaluate the political circumstances that gave rise to these debates from a historical perspective. The study employs document analysis as its method. Accordingly, reports in the ḥadīth literature concerning the Umayyads’ violations of the designated times for Friday and ʿaṣr prayers are examined within the framework of content analysis. The findings indicate that Umayyad rulers’ neglect of prayer times and their excessive prolongation of khuṭbas were subject to criticism by contemporary fuqahāʾ and muḥaddithūn. These practices appear to have facilitated the emergence of alternative religious responses. The transmission of these reports through multiple ṭuruq and their formation within distinct political and historical contexts demonstrate that an accurate understanding of such narrations necessitates not only reference to historical events but also the interpretive insights of scholars specialised in ḥadīth studies.