In recent years, many organizations have been confronted with cloud computing deployment decisions. One critical decision is to balance between discontinuation of in-house systems and adoption of cloud computing systems. Previous researchers usually investigated the determinants that influence cloud adoption only from a new IT adoption perspective. However, when a firm makes its decision to replace or upgrade the existing IS structure, it needs to consider two things at the same time: whether the existing system may fit future development and whether the new system could meet the organization’s requirements. This research seeks to alleviate this research gap by investigating cloud deployment behaviour within an organization from the perspectives of both existing structure discontinuance and new technology adoption intentions. To provide new insights into the cloud computing decisions and the existing adoption theory, a number of hypotheses are developed based on the TOE framework, Upper Echelon Theory, and the IS discontinuance literature. A survey will be conducted to collect data and test the proposed hypotheses. The findings of this research are expected to offer a deeper understanding of transformation from in-house systems to cloud computing systems.