This paper explores the mobile payment phenomenon from SME perspectives in the Kenyan retail sec-tor. Following a qualitative approach, and in-depth interviews, the study concludes that the contextual challenges of Kenya have rendered other forms of mobile payment such as making contactless pay-ments, unknown. However, when other mobile payment options were made known, there was strong support for proximity mobile payments. The findings show that the introduction of any alternative mo-bile payment option in the Kenyan context would be a challenge against the stable trusted way of con-ducting mobile payments. It is recommended that strategies for building trust and customer awareness and adoption of alternative payment methods; be prerequisite towards new and alternative mobile payment options by retailers. The findings show how mobile payments, such as Lipa na MPesa have become institutionalised in the Kenyan SME structures; and how SMES themselves mobilize to legitimize mobile payments. Addition-al results show that Kenyan retailers are strongly driven by customer’s attitude, perception and will-ingness to adopt new payment methods. They identify mobile network reliability as a challenge and indicated that degradation in service levels resulted in a bad customer experience as it led to confu-sion of a transactions success.