One of the world’s largest humanitarian crises that have been going on in Yemen for the last ten years has highlighted the growing tensions within its society. To better understand the rising antagonism between the North and the South, it is necessary to analyze the significant historic events that influenced the development of the Yemeni identity. For the inhabitants of South Yemen and Hadramaut, many of such events took place in the first half of the sixteenth century. The following article presents an analysis of these events focusing on the available Yemeni sources, especially the “Tārīkh al-Shiḥr wa akhbār al-qarn al-‘āshir”, the annals by Muḥammad b. ‘Umar al-Ṭayyib Bā Faqīh al-Shiḥrī (d. 17th cent. AD). The comparison of this chronicle with other sources reveals how the clash between Hadramaut, the Portuguese and the Ottoman empires, as well as an attempt by the Kathīrī Sultan Badr Bū Ṭuwairiq to establish a centralized South Arabian state, caused deeper integration of this region into global politics. Ironically, it was the Sultan’s loyalty towards the Ottoman Empire meant to ensure the rise of al-Shihr as one of the main trade centres of the Arabian Peninsula that soon contributed to its decline. Lastly, the sources reflect the spread of firearms that had an impact on the stratification of South Arabian society and gave more power to the tribes, allowing them to subjugate the sultans, thereby preventing the creation of a unified state in the following centuries.