Is there an example where something has gone wrong because of poorly explained cybersecurity?
I would say probably every single social engineering attack that has been carried out can be at least in part attributed to a lack of explanation. Say you find a USB stick lying on the ground. The first thing that you do, because you're a good person, is you plug it into your laptop in order to find out if there is some information on who it belongs to. Well, that USB stick has been loaded with a virus, and the moment you plug it into your laptop it causes mayhem! So we need to explain to people that actually, even though your first instinct would be to help, probably the best thing is to pick up the USB and hand it to the lost and found.
I always make this example: when I bought my first mobile phone, it was a few centimetres thick, and it came with a manual that was even thicker. These days, you get smartphones that are relatively thin and no manual at all! The idea is that they are plug and play. This might be the case for digital natives, but it's certainly not the case for some senior citizens.
Now the trick is, what is the right level of explanation? You can't bombard people with a 200-page manual that details every single step of how to make your system secure, because people won't read it! But at the same time, you can't really say, okay, now you're on your own, deal with it. You need to find the right level, and you need to find the right language, which will change depending on who you're talking to.