I'm not saying that it's the case for you, but a lot of time I've seen that this actually means "engineers aren't able/willing to talk with management to justify the value of maintainance and make a concrete proposal of how to go about it".
But then again, some other times management just sucks.
Naah, most of the times its that management doesn't want to pay the migration cost. They will keep using a system till it stops producing value, or till adding new things is profitable. They can't give a damn about day to day or what's cool/elegant/maintainable because they don't interact with the innards, ever. These decisions are made with a single equation, if migration cost > new feature cost + maintenance, they don't want to migrate.
Edit: The maintenance isn't a long term view btw. They are not looking at a 5-6 year window where the migration cost slowly pays off. They are worried about optimizing the next quarter.
We upgraded from Rails 4 to 5 last year (lol - it was EOL before our migration was even done), but that was before our CTO left to be a CEO somewhere else and there's been no attempt to find a replacement. Now the executive is obsessed with piling on features with little regard to technical debt or maintenance. It's going about as well as you'd think.
I’ve been lucky to have been working in smaller companies where I’ve been able to communicate the issues with that.
I can’t imagine working in a place that doesn’t want to listen to its engineers or experts. (The same works the other way around too: engineers not willing to understand the business context)
It also likely means no one in management understands building software.
It's tiring when every line of code needs a value proposition and a clear use case. Some things don't take much work to improve/maintain but are next to impossible to slap a $ value on.
But then again, some other times management just sucks.