The mathematics education community has long emphasized applying wordproblem tasks in mathematics classrooms to foster understanding of mathematical concepts. As such, teachers of mathematics are eager to expose students to wordproblem mathematical tasks. However, students find such mathematical tasks particularly challenging, leading teachers to avoid implementing such wordproblems in classrooms. This study investigates the reasons behind the challenges that face students when working on word-problem tasks. The researcher applied a short questionnaire followed by interview sessions. The results revealed that students' inadequate skills and negative attitude towards mathematics led to increased difficulties in solving such tasks. Unaddressed, these difficulties result in increased stress and anxiety in the classroom, and eventually develop into a fear phobia of world problems. The findings also revealed that teachers must understand the importance of such tasks so they can commit the appropriate time and effort into its application. The study recommended having meaningful, handson, reader-friendly tasks that are relatable to students' lives and that are relevant to their interests.