I Fully understand that money involved could seem (and would be) a huge investment, but if it breaks... tons of money will be involved too.
Fortunately, these plants I am talking about are food plants (yoghurt, pudding, and such), so the risk of some foreign government wanting to shut down that plant is rather low. ;-)
And the risk of becoming infected by drive-by malware is contained by not letting these machines talk to the Internet. (There is one connection to the regular corporate network, which does have Internet access, to tell the ERP system how much of each ingredient is left so the Purchasing department will order new ingredients on time. But in my benevolent imagination that connection is one teeeny-tiny hole through a humongous firewall.)
There are alternatives to this problem but many companies don't have the budget, don't want to invest, or don't know that these drivers can be rewritten to new platforms with reverse engineering.
Even so, there are formal ways to show you are solving a problem with certain probability. These kind of projects require extensive testing.
(Hell, I've been at one plant where PC side of the automation still ran on NT 4.0! The customer is reluctant to replace that machine because the interface to the plant automation is a freaking ISA card, and it has become rather difficult to procure a motherboard with an ISA slot.)
It's easy to tell people to update, but in some cases it's just not that simple. (OTOH, the plants I know about are not connected to the Internet.)
And don't get me wrong, I totally agree that it would be better in so many different ways if these machines were upgraded. But some users basically have no choice.