The era of Imam Hassan Askari (a.s.) is considered a special moment in the history of Shiism, where the The present article titled "Challenges facing the Shiites during the era of Imamate of Imam Askari (AS)" was written with the aim of discovering, describing and emphasizing the typology of challenges. To achieve this goal, the method of documentary and analytical studies among ancient and first-hand historical texts has been used. The age of Imamate of Imam Askari (AS) is a special period in the history of Shiism. Strict restrictions for Imam Asgari (a.s.) and the Shiites and the approach of the age of occultation have added to the sensitivity of this age and the importance of knowing the situation of the Shiites. The findings showed: According to the political and social contexts of that era, the Shiites faced many challenges that the delay of some Shiites in recognizing and accepting the Imamate of Imam Askari (a.s.), limitations in communication and face-to-face meetings with the Imam, despite the wide presence of Shiites in different regions, approaching the period of absence of Imam Mahdi (a.s.), facing Shiites with numerous Shiite and non-Shiite theological differences and religions, deviance of some scholars, political pressures and imprisonment of some Shiites, as well as economic hardships, have been some of the most important challenges