Organizations follow diverse approaches to maintaining their operating systems.  Interim patches and service packs continue to modify the OS over time, and much of the operational focus for IT is on maintaining compatibility of applications against these ongoing changes.  In addition to OS management, application management can have an impact on the ability to adapt to operating system changes.  Where application packaging for Windows Installer is actively pursued along with automated distribution systems, organizations are more able to manipulate the applications and resolve application issues when they occur as a result of OS changes.  In addition, processes that classify applications in terms of type and importance, and systems that test the impact of change, all contribute to the ability to minimize the impact and risk of changes.

In general, older applications or those running on older operating systems have more potential issues against future releases of an OS.  The Microsoft OS environment has gone through significant change from Windows 2000 to Windows 7, and organizations moving from Windows 2000 to Windows 7 can anticipate a greater need for remediation than those moving from Windows XP SP2 or later.

Ultimately, the combination of strong application management processes and which OS version you are starting from affect the degree to which a Windows 7 upgrade may impact your organization’s readiness to migrate.