Purpose: This paper aims to explore how AI-based digital shopping assistants can be used to prompt and enhance the Diderot effect in online shopping settings. The main aim is to investigate the effect of psychological factors, personalization strategies and design of the virtual environment on consumer purchasing behaviors and satisfaction in the AI-enhanced e-commerce systems. Within digital retail conditions, with high competition and constantly shifting consumer demands, and the necessity of individual experiences, the psychological processes that underlie AI-based shopping behaviors are the key to business Success Design: The present study involved a quantitative research design that relied on structural equation modeling (SEM) to test more complex relationships between product characteristics related to AI shopping assistant (feature), psychological triggers, and consumer consequences. The study design was that of a primary data survey that included a set of structured questionnaires that were sent to various online stores, which included 847 online consumers aged 18-65 years who were familiar with the AI-based recommendation systems. Findings: The investigation demonstrates that AI-driven digital shopping assistants are potent amplifiers of the Diderot effect, and the enhancement of the psychological factors are the most significant predictors of AI shopping provocation ( =0.623). The research confirms that AI purchase triggers act as the key mediators that have a substantial impact on the level of Diderot effect ( 8712 ) and increase customer satisfaction at the same time ( 0.576 ). The quality of virtual environment design, the quality of recommendation algorithm, and the amount of personalization are all important factors that contribute to the success of AI-based shopping experiences.Originality/Value: The paper is the first comprehensive empirical study of how AI-based digital shopping assistants can strategically use the Diderot effect in online retail setting and provides new insights into the psychological processes involved in the development of complementary purchase decisions in online settings.Research Type: Empirical Research.