Background: Retailing through Virtual Reality (VR) is faced with a dilemma of potential customers using the VR to look for products online, but somehow do not make a purchase online and prefer to visit the physical stores instead. This phenomenon is referred as Transition Risk. Aim: To develop an understanding regarding the concepts and factors that influence the occurrence of transition risk by using UTAUT2 framework. Identify those concepts and thus be able to assist retailers in diminishing the transition risk gap. Methodology: Is a quantitative study that involves an experiment followed by a questionnaire as the research instrument. The data was analyzed through regression analysis by using SmartPLS 3.0 as the data analysis tool for SEM. An exploratory research design for the cross-sectional study of a small sample of 45 people experimented. Findings: Findings of the research suggest that transition risk has a direct relation with the UTAUT2 constructs: performance expectancy, effort expectancy, facilitating conditions, social influence, hedonic motivation, and habit of the consumer. Moreover, absence of familiarity with VR retailing, social influence and consumer’s habit of web-rooming and retail therapy are significant contributors towards transition risk. Furthermore, UTAUT2 framework can also be used to identify reason for no usage and/or abandoning of use technology.