This study investigates the alignment of a firm’s information systems and the viability of three relatively new convergent business strategies - Hospitel, Long Stay, and Homecare Service - in private hospitals and hotels in Thailand. Data were collected from small and medium sized, as well as large and publicly owned, enterprises. In addition, in-depth interviews were done with software vendors who specialize in hospital information systems and property management systems. The results consistently show that the Hospitel strategy is more viable for hospitals and the Long Stay strategy is more viable for hotels. Homecare Service is the least viable strategy for either business. Smaller organizations appear to more readily embrace these convergent business strategies than larger ones. Regardless of the size, both hospitals and hotels perceive their information systems to be in alignment with these convergent business strategies.