I have seen this kind of reoccurring behaviour in two types of people.
People on a certain kind of medication. And people on the spectrum.
I am sure there are other examples I just wondered if ruby has been referred for behavioral or learning assessments.
I suspect something along those lines as there has been mention of a case worker or similar previously.

I just feel like we are expecting behaviour that would be within normal boundaries of someone who has no concept of what that is. Nor does she have the capacity to understand what regular social boundaries entail.

Yes she says the words, but they are in a parroted fashion, like you would expect from someone who is repeating what they have been told without really understanding them.

I might suggest that if advice is to be offered to bear in mind that it's highly likely Ruby has significant limitations to her understanding of deeper complex social situations.
Probably explains why she is cycling through a handful of work places who are familiar with her situation.

Just a thought.