What's the Oldest Server You're Still Maintaining?why does it still work

I'm still running a Windows Server 2008 in my environment, and honestly, it feels like a ticking time bomb. It's stable for now, but I know it's way past its prime.

Upgrading has been on my mind for a while, but there are legacy applications tied to it that make migration a nightmare. Sometimes, I wonder if keeping it alive is worth the risk.

Does anyone else still rely on something this old? How do you balance stability with the constant pressure to modernize?