This study examined the challenges and issues faced by teachers and parents related to the transition from face-to-face instruction to online instruction. During the COVID-19 pandemic, ten teachers and ten parents from the United Arab Emirates (UAE) school system were interviewed to reveal their challenges in managing online teaching and learning. According to the findings, both teachers and parents encountered several problems. Teachers faced challenges such as the need to adapt their teaching strategies and techniques to the new situation, the need for technical support to facilitate the teaching-learning process, the lack of students’ in-class participation and genuine motivation, and the nature and format of the teaching platform, and the fact that they need to have a high level of experience in using technology to serve their students well and engage them in interactive classroom activities. Parents reported several challenges, including lack of experience with the online learning platform, unwillingness to work with teachers to use the online learning platform effectively, lack of experience in properly preparing their children to participate in active online instruction, and multiple children attending different classes at the same time. These challenges place a great burden on parents who must support their children in the younger grades.