With Windows you have a centrally managed OS, but many people install the odd utillity or find stuff packaged in by the main software and hidden in theapplications main program folder (Java, Tomcat, python, WinRar, 7-zip, a Chrome add on from the store because it synched your profile....) then completely forget about it and never update it or don't update the application. So when you have this mentatility applied to an OS you are so going land the brown smelly stuff at some point.
With out mechanisism to maintain all these odd bits of stuff and libraries etc and some decent reporting tools you have not got a hope.
Companies don't understand that just because Linux is free to install no OS is free to manage and maintain. Linux is probably more complex in this regard than Windows or other Unix type OSes as it so customisable and the installable applications often have many open source components that you need to keep on top of.