Most versions of Windows provided some type of software analysis. Businesses might a unit break on software, but the overall cost can be several thousands of dollars. As for hardware a network printer for a business is most likely a long term lease and the cost to break it can get to be quite expensive on 500 printers. Since many large enterprises have custom built applications, Microsoft has not tested them and the organization needs to perform extensive testing. I just found an issue because of a Windows 7 upgrade in June where the UK office is using the European date format (mm-dd-yy) to enter data into one of our databases instead of the U.S. standard that the application was written for (dd-mm-yy). This results in date for some entries on July 7, 2012 to be listed as occurring on December 7, 2012. Can you foresee the problems this can cause in an accounting or tax system that need to report date a quarterly basis?
The firm I work for has also had a number of employees upgrade to Windows 8 without permission and they are now encountering a number of problems that the firms support team is not prepared to handle.