It is widely accepted that digital transformation enables businesses to develop the capabilities necessary to turn weaknesses into strengths. These capabilities are required to take advantage of market opportunities and attenuate the harmful effects of threats, especially in times of turbulence. However, most of the research in digital transformation does not apply to smaller firms and the marketing capabilities created during the ongoing era of the information revolution. This chapter presents new technologies incorporated into SMEs and how they optimise marketing practices and strategies. However, several perils may threaten SMEs’ efforts to adopt digital technology in marketing. This study identifies potential perils from a consumer perspective and comprehensively analyses different aspects of consumer skepticism toward SMEs’ digital transformation in marketing. This can assist future research in studying these challenges in a holistic perspective. This study also presents solutions for SMEs to overcome consumers’ skepticism toward SMEs’ digital transformation, which will help lead them through successful DT.