An administrator is updating drivers?

So maybe not a developer job at all, updating means installing not coding? And the Windows 3.11 on the train has not decent networking or remote maintenance system it needs to be done manually somehow?

But then it's a remote position.

Doesn't seem to make sense to me. But running something as unreliable as Windows 3.11 in a production environment does not seem to make sense anyway.

Some say recertification of a new system would be too expensive. But if this system is certified, I'd say it's a certification theater not worth the paper it is printed on.