An apparatus comprises a processing device configured to receive, from a given host device in a given data center that utilizes a given piece of software, first configuration information associated with the given host device. The processing device is also configured to identify available software upgrades for the given piece of software and to select issue indicators associated with installation of the available software upgrades on other host devices. The processing device is further configured to provide, to the given host device, a recommendation to install the available software upgrades for the given piece of software on the given host device responsive to determining that (i) the first configuration information associated with the given host device has at least a threshold level of similarity to the second configuration information of the other host devices and (ii) the issue indicators have at least a threshold issue criticality level.