Rolling upgrade is a widely-used industry technique for updating software while a service, that is provided by multiple instances of the software, remains available. In cloud deployments of software, it is usual to implement the update step for rolling upgrade by replacing entire virtual machine instances. During the process of rolling upgrade, various failures may occur due to the complexity of software stack and the uncertainties of the cloud platform. Instance health checking and replacement are standard functionalities in most cloud infrastructures, though these create uncertainty in the duration of the whole upgrade procedure. In contrast, software and configuration errors are not usually detected by infrastructure functionalities, and if these happen, the entire rolling upgrade normally is unsuccessful and the system is left in an unsuitable state. In this paper, we propose an approach, named R2C, which innovates the stat of the art with our early error detection and predictability to increase the robustness of rolling upgrade on cloud platforms. We evaluate our techniques through real life testing in Amazon Web Service (AWS) and through a simulation.