Recent years, offshore outsourcing has received large amount of attention from both industry and academia because of its attractive advantages such as cost reduction, talent access. As an alternative way to implement information systems in operation management, offshore insourcing has been greatly overlooked. Though organizations shun from the contractual obligations in offshore insourcing, they are still encountered with plenty of thorny decisions and communications because of the do-it-yourself nature, especially in the onshore-offshore migration process. To investigate how organizations can well deploy offshore insourcing, we employ a theoretical lens of knowledge boundary spanning and organizational learning to examine a successful offshore insourcing case. Three types of organizational learning capabilities have been identified to span the increasingly complex knowledge boundaries. Both theoretical and practical contributions are discussed.