1. A computer implemented method of dynamically recommending changes to an association between an operating system image and an update group, the method comprising: monitoring, by an image deployment monitor, a configuration of a deployed copy of a first master operating system (OS) image, the deployed copy associated with a first update group of the first master OS image; detecting, by the image deployment monitor, a modification in the configuration of the deployed copy; determining, by the image deployment monitor, that the configuration of the deployed copy with the modification more closely matches a configuration of a second master OS image than a configuration of the first master OS image; in response to determining that the configuration of the deployed copy with the modification more closely matches the configuration of the second master OS image, generating, by the image deployment monitor, an association recommendation that recommends associating the deployed copy with a second update group of the second master OS image; and associating based on the association recommendation, by the image deployment monitor, the deployed copy with the second update group of the second master OS image instead of the first update group of the first master OS image.