In order to provide better customer services to its rapidly growing users shopping online, retailers harness AI chatbots to solve issues around service provision and communication. This paper reports on an exploratory study that investigated obstacles and challenges affecting continuous engagement in conversational AI. 15 interviews were conducted to gather in-depth insights and diverse perspectives, and the qualitative data gathered was evaluated using a theme analysis technique. The findings revealed three types of avoidance behaviors as well as a collection of 14 critical hurdles associated to various technological, interactive, readable, psychological, and experiential components. Among them, psychological barriers were recognized as the most crucial. This challenge was triggered by a range of technological obstacles, user interaction obstacles, readability obstacles, individuals' experiential obstacles, and technological obstacles is the underlying causes of psychological, readable, and experiential obstacles.