I guess this entirely depends on what country you're from. I'm a developer, and I constantly have to deal with ignorant bosses. They push me to write code faster, sacrificing proper planning, architecture, and testing. Then I'll be the one sitting up all night fixing a broken release, because my code doesn't work.

As the professional in this scenario (the one who knows how to develop software), it's my responsibility to make sure it's done right. My boss isn't supposed to know how to do it, so it's my job to let him know.

Of course, you still have to have your bosses permission to do it, so I totally agree with OP putting pressure on the boss. It's important that the boss knows what's at stake, and it's OP responsibility to make sure he does. But at the same time, it's important for OP to know why the boss doesn't want to upgrade, he might have a good reason, or at least it would be easier to argue against.

Again, it probably depends on the country. I work in a country with high job security, but it might be different in other countries (not the responsibility, but the danger of doing your job properly).