Let's pretend you want to attack a company.
First you scope out attack surface. If you can physically penetrate security there are all manner of attacks you can accomplish and connectivity you are able to achieve. You might go to a search engine like shodan (https://www.shodan.io/) and discover some internet exposure that is attackable. You might find e-mails and start phishing/landing trojans. You might be able to execute a supply chain attack (ala solarwinds). You might be able to compromise an employee. After you compromise the corp network you might figure out how to escalate into the infra network.
Now you are a company. You have limited resources. Security is not your business. Security is only a "cost." Tech isn't your main business so you need to hire a security minded person without a strong ability to vet them. That security person needs to scope the attack-able surface, model the above risks and more, and implement preventive measures. That person will probably be hired well after infrastructure is already established. That person will have to justify the potentially large resource expenditures involved in solving problems and hiring more security engineers. That person will be a very limited resource and therefore very expensive since our universities don't pump out a lot of security experts. This person will probably have a market rate of well over 300k a year. That person's competence will likely directly correlate to time spent in industry, so new grads probably wouldn't cut it. Maybe you decide to see if companies will sell you solutions to this problem. How do you separate those selling security theater from those who will legitimately solve your security problem?
So, if you are the business owner at what point do you decide, "wow, we need to spend a lot of resources (time, attention, and money) on security." After some number of employees? After some dollar cost in business? After some position in industry? When a competitor is breached? Unfortunately the de facto answer appears to be after the first major [embarrassing] incident.
Imagine you appear to have had impeccable security and are spending 10 million a year for it. How do you know you are making good on your investment? How do you know 5 mil isn't good enough? How do you know you haven't already been deeply breached by a very competent APT?
Unfortunately, the reason we haven't solved the tech problem is that it is an arms race. This stops the problem from fundamentally being a tech problem, but instead a problem of incentives.
Taxing poor security via government run pen tests with fines (forced bug bounty), that grow as the number of vulnerabilities are found is a system that might change incentives. Indemnification for (maybe only accredited) white hats might change incentives. Regulating all companies to be part of a bug bounty program might change incentives. Legally requiring breach insurance might change incentives. Alternatively there are probably small fortunes to be made to the first entity able to solve corp net as an economies of scale problem (AWS for corpnet).
To answer your question directly. We currently have a system where the average business owner is either uninformed, ignorant, or has calculated cost to be greater than risk, resulting in lower resource expenditure than required to solve these technical problems resulting in poor security that directly puts national security at risk.