After some random thinking about the show, and Jack’s powers. I think I came up with a theory as to whats happening. For starters, I do believe Jack can use his powers independently, but I think others can use his powers too. i think I can explain this to make sense. I hope!
The first time we see Jack use his powers, when he isn’t scared, is when he’s with the Sheriff’s son and making the candy fall from the machine. He says he doesn’t know how he’s doing it, but I think the boy is unknowingly using Jack’s powers for what he wants... the candy.
Before Jack was born, while still in the womb, Cas connected to him and killed Dagon. Dean asked what “that” was, and Cas said “It was me... and also him”
Sam (while they were both still in jail) asked Jack what it was like when his powers were used and Jack said “It is like Im me, but not me” - is this the other person using the power? Is it Lucifer using his powers through their connection?
Later, Asmodeus has Jack opening a portal to Hell. Jack tells Sam while he can’t move a pencil, that it was like Asmodeous was making him do it.
When the boys were at the therapist office and Jack and Dean were cuffed, Jack couldnt open the cuffs, BUT when Sam got there, Jack threw the shifter into the wall, and made the bullet miss Sam. Now you know Dean wanted Sam safe much more than he wanted to cuffs open, so he could have unkowingly, utilized Jack’s power simply by wanting to save Sam badly, and Jack wanting the same.
And the big one (not in chronological order) is that Jack awakened Cas. But was it because Jack wanted it, or someone else did and used his powers with, or without knowledge? It could be that Sam or Dean or both in that moment wanted Cas back, and Jack was probably in agreement, since he was listening to the argument, Another possibility is that Lucifer used Jack, through their connection to wake Cas up. We know that soon Cas starts working with/for Lucifer, so is the connection there already?
when I speak of a “connection” between Lucifer and Jack, Im talking about how Lucifer could always tell Jack was still alive and growing and somehow, even in the AU, Lucifer knows Sam and Dean have him. We havent seen Lucifer for a while so who knows whats going on on that end.
So if this is the case, it sees that Jack needs to want the same thing. He would want the candy, he would want to open Hell by the way Asmodeus was telling him to do it for God and such. He would want to save Sam, and he would want to see Cas. So its somewhat non-consentual but not entirely. If Jack didnt want to move the pencil, because he was scared of his powers, or because it was the “opposit of fun” he wouldnt be able to move it.
So maybe its a matter of influence. Lucifer and probably Asmodeus could already know this of Jack, if Lucifer is already working through him sometimes, and the way Asmodeus knew what to say to get Jack to perform.
This could get very messy. It could rest on who has the strongest influence, and what Jack wants most, but Im pretty sure at least one of the bad guys can control Jack’s mind as well. Even if its only when they’re near him.
Lets ponder this, shall we?