Despite the recent rapid development in chatbots, reaching their full potential in the realm of e-commerce remains a challenge due to poor usability and lack of trust between humans and machines. To address this gap, the study addresses three key questions: whether current e-commerce chatbots follow established design principles (RQ1), current landscape of users’ attitudes towards chatbots and factors influencing their engagement (RQ2), and the impact of chatbot personality on user satisfaction in e-commerce interactions (RQ3). Findings through explorative review of existing chatbots, an online questionnaire, and user study highlight the small percentage of chatbots currently following established guidelines, varied opinion of users across a range of demographics, and minimal impact of personality on a buyer’s purchase decision. The results identify that designers should prioritize adherence to established guidelines, emphasizing the incorporation of visuals, transparency via clear descriptions or source links, and build long-term rapport with users through persistence in information retention. Offering the ability to configure customizations may also lead to a higher user satisfaction and repeated usage, with the ultimate goal of better meeting consumer demands and enhancing their overall online shopping experience on e-commerce platforms.