Software has become very important in everyday life. It is used in almost every field. Even in local society, the dependency level on software has also increased. Whenever there is a software failure, it might have severe consequences on society and individuals alike. Failure does not only affect the client but also the company that is responsible for the development. This study aims to explore the issues that face users and investigate the factors that cause software to fail. A questionnaire was built to derive the issues that users face and distributed using an online Google form across twelve organizations in Benghazi, Libya. In addition, ten interviews were conducted with twenty developers to identify the factors that cause failure. The most common factors among interviewees were identified, including unrealistic schedules and budgets, a lack of user involvement, and incomplete requirements.