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@Narf,

I agree with you but every developer may not be in a position where they can come in and make drastic changes (unlike you and me =) ).  Sometimes it has to be baby steps. I'm quite sure both of us has many stories we could tell where it was so obvious that an upgrade was needed but management was being a pain and didn't fully understand the impact (I even worked on a project where I was more experienced then the Team lead and had to indirectly lead the team and upgrade the code).  In those scenarios you have to do what you can until you can get to the point where the software can be made current.  That is why sometimes it worth saying hey do this at least until you can do that.

It's an update, not a rewrite - there's nothing drastic about it and management shouldn't even be asked about this. The only reason management becomes a PITA with this is because when you ask them how to do your own job, they assume it's a big deal with meaningful impact on business operations (oh have I got many stories about that, indeed).

Let me tell you about the last time I updated CI for a company ... Granted, knowing CI inside out, this should be like a walk in the park for me, but even if you double the time it takes, it's no big deal for anybody.

They were running 2.0.something, with a bulk of custom patches on top of it (some of those, they claimed was for specific stuff that CI couldn't do, which was false - they had shot themselves in their collective foot for nothing). That wasn't one small-to-medium size project, but 3 separate ones, each having at least 100 controllers. Copy-pasta all over the place. And I don't use IDEs, so I couldn't do my colleagues favorite "global search and replace" - every single change, done by hand, not even auto-complete.

I spent 2 days extracting those custom patches into extensions, and completely reverting the parts that were no longer necessary, then the upgrade itself took 3 hours.

Seriosly, it takes more time to QA than to actually do it. There's no excuses.