An apparatus comprises a processing device configured to detect that a given software upgrade is available for a given computing device, to identify other computing devices on which the given software upgrade has been installed that exhibit at least a threshold level of similarity to the given computing device, and to determine whether any issues were encountered on the other computing devices as a result of the given software upgrade. The processing device is also configured to generate a recommendation as to whether to initiate download of the given software upgrade on the given computing device based at least in part on whether any issues were encountered on the other computing devices as a result of the given software upgrade, and to initiate download of the given software upgrade on the given computing device based at least in part on the generated recommendation.