Re: Back in the mid-1990s. . . .
"In this case, I would want to to bill the misused CD to the training department, for failure to teach the general what the bits of a computer did."
On the whole I agree with you but maybe you missed the fact that the general had signed a waiver.
It's difficult if not impossible to deal with idiocy that's risen to the higher levels of an organisation. After all these are the people who should be exercising wisdom and laying down rules for the rest of the organisation. The first step of this should be understanding why those rules are needed and why they apply to themselves* as much as everyone else.
*It's doubly important that they follow their own rules. They need to set an example.