So imagine - you're relying on some piece of software released around 2005. 2.6.10 Linux kernel, ext2 (maybe reiserfs?) TLS is called SSL and you're good if your DSA key has 512 bits... This essential service your company needs had long been abandoned and all attempts to mitigate the imminent disaster have failed. (Migrate to competitor, revive the code base, run in a VM)
... Or some CTO has seriously done a bad job anticipating whatever maintenance necessary over last decade.
I appreciate that change is hard sometimes, but maaaan life is so much easier if you upgrade/migrate/rebuild every now and then with some frequency.