If no one bucks up and tells management that the dev environment is a blocker in the first place, how do they know? I've seen way too many co-workers sit and stew in silence about problems that get solved as soon as they start speaking up, or at the very least start getting factored into estimates once someone starts saying "hey this sucks and adds 3 days to every week of work". Maybe it never gets fixed because "reasons" but it at least stops being an "unseen" problem.
I worked on a team that used a free tool as part of the dev process that was just a continual source of problems for about half the team, with no obvious reasons why. Every 4th or 5th launch of the tool would just fail, and you'd lose half a day to trying to resolve the problem or otherwise clear all the settings / caches / accounts and start from scratch. Yet the team had worked like that for a handful of years because "it's just one of those things". It took 2 days after bringing it up to management to get the whole team paid licenses to an alternative tool. No one had bothered to bring it up because no one thought management would pay for a tool when a free one worked. But a half a day lost to a tool failure cost the company an order of magnitude more than just buying licenses to a better tool.
I worked on a team that used a free tool as part of the dev process that was just a continual source of problems for about half the team, with no obvious reasons why. Every 4th or 5th launch of the tool would just fail, and you'd lose half a day to trying to resolve the problem or otherwise clear all the settings / caches / accounts and start from scratch. Yet the team had worked like that for a handful of years because "it's just one of those things". It took 2 days after bringing it up to management to get the whole team paid licenses to an alternative tool. No one had bothered to bring it up because no one thought management would pay for a tool when a free one worked. But a half a day lost to a tool failure cost the company an order of magnitude more than just buying licenses to a better tool.