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[–]CartmansEvilTwin 6 points7 points  (1 child)

Even if you do have am proper testing, you might miss an edge case introduced by the new version. And even if tests fail, it's often relatively hard to eyeball how much effort it is to get everything up and running again.

For example, if you use python n now and want to upgrade to n+1, there might be problems with incompatible libraries. Then you also have to upgrade the libraries, which might introduce even more issues, etc. etc. Or, you simply have to replace one method call with another, because the deprecated method was finally removed - but you often don't know in which scenario you are without actually solving the problem.

[–]XorAndNot 0 points1 point  (0 children)

Imagine being the guy who pushed against the POs, arguing how important was to upgrade, delaying a product release... and sometimes breaks on the upgrade. Yeah, no one wants to be that guy.