It seems daft to keep seeing this lesson being learned by tech companies, and keep seeing blog posts where most of the pain would have been handled easily by just making upgrading a key feature.
Instead, tech managers and engineers seem to make the same mistakes over and over again, delaying those upgrades, until suddenly they discover it's a hard task to upgrade. I get delaying to _some_ degree, it's better to let other people figure out those sharp bits on the bleeding edge for you, but you need to set an explicit target for upgrading.
At another large tech company I worked for, it took the security team swinging the sledgehammer to get teams to upgrade from known-vulnerable versions of Ruby on Rails. When they came to do it, they discovered the changes were so extreme that the effort involved in migrating was likely more than the effort involved in a complete re-write (they did at least have pretty comprehensive tests)