Digitalization has the potential to transform economic transactions through the extension of customer reach, increase revenues, improvement in quality of services, and enhancement of the management system. However, its relevance and necessity do vary across cooperatives. This study explores why some cooperatives are still reluctant toward adopting digital tools, using a mixed-method approach through a survey and interviews conducted with 20 cooperatives and their members. Key findings point to the low level of acceptance of digital technologies among the targeted group, in conjunction with a continued reliance on more traditional “word-of-mouth” marketing channels. At the same time, many cooperatives recognize clear added value arising from digitalization, including efficiency gains in operations, enhanced coordination, new marketing opportunities, improved access to information, and enhanced traceability. The study points out that through digital transformation, cooperatives can be much more competitive, greatly contribute to regional socio-economic development, and thereby be more sustainable in the long term. This study explained the implication of this reality concerning the sophisticated way of conducting digital adoption, considering the specific contexts and clientele of cooperatives.