The need to create and maintain industrial peace, in one hand, protect the fragile interest of workers on the other side to boost economic development have been critical issues which have attained significant consideration from states. To that end, they introduced at international and national levels different set of legislations regulating employment relations. Among other things, working time limit has meticulously been introduced to safeguard the rights of workers, who are generally with the lesser bargaining power, and make the labor more productive. Ethiopia has accepted this notion of delimitating working hours, and adopted legislations. However, it has become a public secret that such rules have not been maintained in practice and that the enforcement mechanism appeared meager. Though researches have been made in different part of the world; in Ethiopia, particularly in Dire Dawa, the factors contributing for long working hours have not been addressed. There are, however, indicators that particularly waiters are working for longer hours than what the law stipulates. In a town dubbed as industrial corner, this factor should not be left unconsidered if the aspired objective of the labour regulation is really to be met. This research, hence, took the first step in studying the existence of this violation, and investigating the contributing factors. The data were collected through structured questionnaires and interviews, and samples were taken using stratified systematic sampling method. Data were analyzed through quantitative (descriptive analysis and logistic regression model) and qualitative techniques. Then, job insecurity, lack of legal awareness, culture of the work, salary, tips, dependents, and level of education have been found out to be contributing factors, and their level of significance has also been established. It has also revealed that the absence of strong enforcement mechanisms contributed for the apparent non-adherence to the rules so delimiting working hours.