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Bundling has emerged as a key issue in current marketing and online business thinking. By extending contemporary conceptualizations, this paper proposes a new approach to bundling for both marketing of products and services in E-commerce. It reviews the literature on both bundling and consumer product evaluations and puts forward a new approach. It demonstrates that contextual bundling can constitute the strategic core of a company utilizing E-commerce for its business; at least if the firm’s primary goal is to maximize the opportunities of attracting valuable customers, online content purchase and its consumption. This research carries forward some results from previous studies, while it finds other prior results to be questionable. Shows that strategic implications of online bundle formulation is only partially explained in terms of a price or product focus, which is where most of the previous research has concentrated on. A context specific price or product bundling focus can have more strategic implications than a simple price or product focus on consumer purchase evaluations. Businesses must define bundling through an indepth appraisal of the actual contextual experience of the customers, rather than focusing solely on reservation prices, which is where previous literature has put maximum emphasis.