Techniques for receiving operational preferences for operating network devices, and determining software updates for the network devices based on the operational preferences. A recommendation system may determine a group of network devices in a device network based on the network devices in the group performing a common functional role or have common attributes. The recommendation engine may further receive the operational preferences for the group of network devices from a user associated with the device network. These operational preferences may be continuously, or periodically, evaluated against actual operating conditions of the group of network devices to determine whether a risk metric associated with the actual operation conditions violates an operational preference. In some instances, the recommendation system may provide the user with access to a recommendation to run updated software that is more optimized for the network device and that satisfies the operational preferences of the user.