The digital transformation of the Indian economic landscape has brought about a paradigm shift in consumer behavior from simple access-based adoption to complex psychologically driven decision-making processes. Despite the exponential growth in the number of internet connections and smartphone penetration across North India, a persistent "Engagement-Conversion Gap" is present in the e-commerce landscape suggesting that the traditional drivers of digital adoption - primarily "Ease of Use" - have lost predictive power. This research paper examines the generational imprints of Generation Z (Digital Natives) and Millennials (Digital Immigrants) in terms of precedents to "Customer Sway" defined as the psychological shift from hesitancy to purchase intent. Employing a quantitative, descriptive cross-sectional research design, the study analyses data of a quota-sampled group of 446 respondents across the National Capital Region (NCR) and Haryana. The study uses validated scales to measure Perceived Value, Online Convenience, Trust and Social Proof. Independent Sample T-Tests show a statistically significant "Generational Trust Gap" (P < 0.001), a huge "Trust Deficit" among Generation Z (M=2.99) compared to Millennials (M=3.52). Contrary to the "Digital Native" hypothesis which assumes an innate comfort with technology equates to trust, the results show that Generation Z has characteristics of "Tech-Skeptical Pragmatism" relying heavily on Social Proof and visual validation over institutional assurances. On the other hand, Millennials exhibit behaviors that are consistent with "Value Optimization" where trust is mediated by institutional credibility and utility. The study concludes that the North Indian digital market has moved into a "Post-TAM Era" where Credibility, rather than Convenience, is the currency of influence, which requires different strategies to address these two different demographic cohorts..