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Or the new version doesn't offer a compelling reason to upgrade, and would require extensive regression testing, potential downtime, and potential lost money fo

Or the new version doesn't offer a compelling reason to upgrade, and would require extensive regression testing, potential downtime, and potential lost money for little to no benefit to the end user. Upgrading core software costs money, upgrading core software just because a new version comes out costs more often. Sure one should test to see if there is a compelling reason, but if there's not, why should one mess with something that already works well?

ubernostrum 11y ago
Refusing to "mess with something that already works" is a recipe for disaster. What companies often learn too late is that there are basically two options: 1. Make maintenance -- both in terms of upgrading underlying software, and addressing accumulated technical debt -- a regular, required part of their process, or 2. Occasionally face a potential existential threat from the unbounded cost of staying fixed in perpetuity to a stack that "already worked" once upon a time but no longer does due to lack of upstream support and available developers to keep it limping along. The genuine problem is that "what does this do for next quarter's results" is the only concern, which means long-term thinking is actively discouraged.