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Based on data collected (n = 67) through the soft-laddering approach, six types of motivation are identified, include Quality of life, sense of accomplishment, Family well-being, Financial security, Self-direction, and Health consciousness. This study sought to address this gap by using the means-end chain theory method to explore the motivational complexity of VS-shopping. With the expansion of virtual supermarket shopping (VS-shopping) consumption, there is an increasing need to investigate the variety of consumers’ motivations for engaging in such behavior. Virtual supermarket shopping has entered a phase of commercial mainstreaming as retailers aim at broadening the customer base, especially in the context of COVID 19 emergence. The paper rounds off with a discussion, implications for practice and future research, limitations, and conclusions. This also has clear implications for branding activities in other social media. This implies that organisations must carefully consider not only the nature of existing brand offerings before entering into the virtual world, but also whether this new channel is indeed a suitable channel in which to be embarking on branding activities. Virtual-world brand value is strongly determined by extension attitudes driven by an assessment of how well the category of the real-life brand offerings fit with the virtual world and how well the real-life brand offerings fit with the three-dimensional virtual-world channel within which they have emerged. The overall research model is strongly supported. A total of 211 matched responses were collected and tested using partial least squares. Data were collected in two phases, both in Second Life via automated avatar survey bots and via a Web survey. While category fit is an established construct, channel extension fit represents a new variable developed specifically to help explain brand transference to the new context. Using axiology, we assess the value of real-life brands in the virtual world and test an exploratory model of brand fit to the virtual world. This paper examines the brand value of real-life brands that have moved to the virtual world of Second Life. Online virtual worlds are rapidly becoming recognised as an important new channel for marketing and brand building.