The retail landscape in Pollachi Taluk is witnessing a significant transformation as traditional cash-based transactions intersect with rapidly evolving digital payment systems. This study explores customers' experiences and preferences toward cash versus cashless transaction methods in local retail outlets. Utilizing a primary dataset of 120 respondents, the research employs a descriptive design to evaluate factors such as convenience, speed, security, and technical reliability. The socio-economic profile reveals a predominantly young, female, and rural-based demographic with high undergraduate attainment. Findings indicate a strong hybrid preference, with 54.2% of respondents utilizing both modes. Cash remains highly valued for its "ease of use" and "spending control," whereas cashless methods—predominately UPI—are preferred for their "convenience" and "speed." Chi-square analysis demonstrates that while age does not significantly influence payment preferences, family annual income shows a significant association with cashless adoption. Despite high awareness levels (75.0%), technical barriers such as network issues remain a primary deterrent for 68.3% of digital users. The study concludes that for a seamless transition toward a "less-cash" economy in Pollachi, retailers and policymakers must prioritize improving digital infrastructure and addressing security concerns to enhance overall customer satisfaction and trust.