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A significant event in the final years of the life of the Prophet Muḥammad was the Expedition of Tabūk. This has been reflected in the Holy Quran and historical texts by including its particular circumstances. In the Expedition of Tabūk, the behaviors and actions of the hypocrites ran counter to the sacrifices and persistence of Prophet’s companions. In response to this situation, the Quranic verses of Sūrah al-Tawba reveal the hypocrites’ intentions, expressing the actual reasons for their lack of cooperation. Given the influence of this group of people on the religious community, it is necessary to elucidate the behaviors and intentions of the hypocrites. This study presents the typology of hypocrites’ behaviors during the Expedition of Tabūk based on the verses of al-Tawba by using qualitative and quantitative methods, and analyzes the causes of these behaviors. The statistical reviews of 39 verses dealing with the hypocrites’ actions revealed that 84% of these actions were sociopolitical and religious, while the remaining 16% were economic. The particular focus of the verses of al-Tawba on the behavior of the companions of the Prophet in the Expedition of Tabūk and disregarding its military objectives elucidates the main goal of the Expedition of Tabūk. This Expedition did not pursue military goals; rather, it was a test of Muslims to reveal the intentions of the companions of the Prophet. It seems that the diversity in the hypocrites’ behaviors is rooted in their attitudes towards religious values and the conflict between the values of the Islamic society with their ideas and purposes.