VersionClimber is an automated system to help update the package and data infrastructure of a software application based on priorities that the user has indicated (e.g., I care more about having a recent version of this package than that one). The system does a systematic and heuristically efficient exploration (using bounded upward compatibility) of a version search space in a sandbox environment (Virtual Env or conda env), finally delivering a lexicographically maximum configuration based on the user-specified priority order. It works for Linux and Mac OS on the cloud.