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This paper will focus on hajj brokers, also known as Sheikh Haji. The hajj brokers system had existed for so long that it is said to be 'as old as the hajj itself'. They had become a part of the hajj sub-culture and tradition for the Muslims, especially Malays. This article aims to analyse the issues and challenges faced by hajj brokers during the sea travel period up until the establishment of Muassasah. The historical methodology is employed in this qualitative descriptive and analytical study. The study uses primary sources such as the Ordinance of the Straits Settlements (S.S)-1906-1907, files from the State Secretary Office and the Annual Hajj Reports. These documents are examined, interpreted, and organised to form objective arguments. The arguments are also supported by secondary sources. The study found that there were various issues related to the hajj brokers' service, resulting in numerous grievances. The issues include misconduct, neglect, and mistreatment of hajj pilgrims by the hajj brokers. At the same time, the hajj brokers also faced many challenges such as stiff competition among themselves, and changes in the rules and policies of the Saudi government. [ABSTRACT FROM AUTHOR]