Evaluating Upgrade Options from Windows 7

When the Windows 10 Anniversary Update becomes generally available on Aug. 2, 2016, Windows 7 will have approximately three and a half years of Extended support remaining. As part of the rapid cadence and continual release model for Windows 10, the Anniversary Update serves as the equivalent to a first service pack—the milestone many organizations use to trigger upgrading to a new version of Windows. Organizations need to decide when continued use of Windows 7 will become intolerable and what client OS they intend to use after Windows 7 leaves support.

When to Upgrade

As a version or major release of Windows matures, a dichotomy is created. On one hand, the aging version becomes more stable because most of the bugs and vulnerabilities are known and a large selection of general and industry-specific applications exist to exploit the OS’s features. It runs on a wide variety of devices, and users know how to use the OS. On the other hand, the aging version can become less stable and secure because as bugs and vulnerabilities are found, it becomes harder to fix problems without affecting other parts of the OS or creating new and often worse problems. New hardware will have features and components not supported by the older OS. In addition, as the focus of the entire Windows team shifts to the new version, the skills and willingness to fix the aging OS decline. However, as Microsoft did with Windows XP, it will likely offer Custom Support Agreements for Windows 7, although such agreements come with significant costs that rise every year, and they may still offer only a limited ability to get reported problems fixed.