For anyone who’s worked in an End User Computing role in at least the last 10 years, application compatibility has been a challenge. The migration from Windows XP to Windows Vista or Windows 7, in particular, was very painful for many. The good news with initial releases of Windows 8/8.1 and Windows 10 is that application compatibility was much less of an issue. Microsoft took more care to ensure that if an app worked on Windows 7, it would also work on the newer desktop operating systems.
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Fast forward to the present day. Microsoft has drastically changed the release cadence for their Windows desktop operating systems with Windows 10. While application compatibility still isn’t as big of an issue as it once was, it’s a challenge that has been returning. Security hardening out of necessity has lead third-party applications breaking and, in some cases, even some of Microsoft’s own products breaking too!
We have to accept that some upgrades are going to result in broken applications, for most organizations, that means pushing Windows 10 upgrades and just hoping for the best. Windows migrations of the past would take 18+ months on average to complete, and that was usually with a large project team assisting. In large part, the time and effort were spent on application testing, but it’s not feasible for day to day IT teams to use the same methodology for the new, more frequent OS upgrades. There just isn’t enough time and resources.
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