I agree, but I wouldn't be underhand and I certainly wouldn't use read receipts. That looks horribly like the very worst kind of arse covering.
You shouldn't go over your boss's head. Juggling a large number of conflicting priorities is what managers are paid to do, and you won't do yourself or anyone else any favours by undermining your boss's judgement in that way. But you should also consider the risk that she consciously has her own best interests at heart rather than the business's interests. She might have the view that, in the event of a security debacle, she will pretend that the team messed up and failed to follow instructions, and simply ride out the storm. In the meantime, she looks efficient and appears to gets jobs done quickly with a minimum of fuss.
Instead, you should sit down with her and clearly express your concerns. You should then follow up your meeting with a very clear email that summarises the conversation. You need to start with an assertive but non-hostile comment that leaves no-one in any doubt what has happened - something like this, "As we discussed earlier, these are the security issues where I believe that we are falling short of regulatory expectations..." Print out that email and take it home with you.
At that point, your boss has three options. 1. She can fix things. 2. She can escalate up the food chain, so that someone bigger than her can decide whether poor security is really in the company's best interests. 3. At huge personal risk, she can quietly ignore you.
Middle managers tend to have pretty strong survival instincts, so option 3 is very unlikely to to fly. Option 2 is pretty likely, and her manager might well say that security is too expensive/awkward/boring/inconvenient. If that happens, you're probably better off working some place else where you can be proud to turn up in the morning.