If I was to answer the question with an opinion - it then brings to my mind, another question.....
Speaking of individually souled people, whether they wake up or not must be a choice, therefore: it is free will. This should encompass whether to 'see' something that's in front of their face (and chosing to ignore it and pretend it's not there), as much as it encompassess the need to do 'the work' in order to 'see' something in the first place. So that seems to me, two types of 'seeing'.
An OP is not an idividuated soul, so therefore it is unlikely that they understand what free will is, or what 'waking up' means for that matter, unless it's a program that 'tells' them what it means, but they won't really understand what it means or it's implications, so they can't do that thing anyway. It would be like asking a cat to understand how 3rd density works. They think it's either magic, or scary/spooky because they don't understand how it works. I guess its pretty similar to how we 'see' the density above us, too.
So my question comes from those individually souled people who chose not to wake up..... (and I'm about to answer my own question here, would you believe it!)
My question would be, by not 'waking up' (seeing what's right in front of their noses), is that person chosing to cycle into entropy? My answer to that would be both "yes" and "it depends on the person".
Because not everybody choses, or has been persuaded to follow the entropic path (I am assuming this because it would be in line with the concept of free will). Some people just might not be ready to 'wake up', at least not in their current lifetime. Others are already awake, but chose to see only what they wish to see. They make a choice to believe an illusion. To me, these are the people who are on the entropic path.
We can use Hitler as a potential example (and only if he uses free will). He was obviously an individuated soul because he has been reincarnated (according to the Cs). So, not a psychopath (broken OP), maybe a sociopath? But never-the-less a deeply troubled individual. In his (or her) new life, will he (or she) chose to go towards STO or STS - by making a choice to see what they want to see, or seeing what is actually there?
It seems to me that this is where free will manifests. But then, we must first have a definition of what "waking up" means. I suppose it could mean the opposite of "going to sleep" and one could only 'chose' to "go to sleep" if one had been already awake first. That would require the exercise of free will. If one was already asleep, then it would require the effort of free will in order to wake up and that would only work with an individuated soul because they would be the only ones who would KNOW they are asleep (and don't see things because of it).
So, with regard to Free Will, I think the concept may have more influence on each of the steps (even without our conscious knowledge) than we realise.