Online channels are highly relevant for microenterprises, but research focusing specifically on the challenges and circumstances faced by microenterprises doing channel expansions is scarce. A channel expansion is a strategic decision that will modify the business strategy of the company. Through twenty-two case studies in Finland and Sweden, we investigate microenterprises doing channel expansions. The goal of the research is to find out how microenterprises carry out channel expansions and what characteristics emerge from the two national samples. We look at the channel expansion from a business model perspective, which gives us a practical tool to probe the microentrepreneurs to discuss their expansions from many dimensions. Our findings show that microenterprises struggle to balance technology, business, and customer demands with competence and resources. A lack of strategic planning leads to a situation where both positive and negative outcomes of the channel expansions are largely unanticipated and unexpected.