Bill Gates is not the problem.
DND's IT infrastrucutre, designed for people with regular access to said infrastructure, is the problem.
Most Army reserve units are lucky to have a 10:1 ratio of pers to computers; and all need access at the same time. That math doesn't work (especially when a simple user change can take over half an hour - can't run many people through when you've got a 4 hour window available), and results in people using work arounds that the IT security gods abhor, but meet the operational requirement.
Thus, yes, I've seen USB sticks moved between DND and non-DND systems. And documents sent out to non @forces.gc.ca email addresses. And any other number of actions taken to keep the machine creaking away because the IM/IT rules were drafted without any understanding of the user situation and reality.