Yep sandboxed apps never break out of their sandboxes, and anything in a VM always stays inside that VM and always plays by the totally bug free rules.
So you think breaking out of a small simulation into a bigger simulation would satisfy? It would certainly be interesting, but, if there are billionaires in the bigger sim, I guess they'd soon be saying, "No ... I meant break out completely." And then you'd be back to facing the original question: does it make sense to imagine a simulated entity having existence outside the simulation?
In The Matrix, the simulation was something experienced by entities outside the simulation. That's a factor on which the metaphisics of "breaking out" depends. Thus, the question is whether, if this is a simulation, are we participating from outside, or entirely simulated?
Do video-game characters have life outside the game? You could say so, in that they have life in our minds. No, it's more than that; they have animate energy in the universe. But if one of them wanted to join our world as a regular individual human, there'd be a problem. You'd want to explain to them, "here's your relationship to what we think of as The World Outside Your World." Similarly, we'd need someone in TWOOW to (start to) explain the corresponding relationship to us.
Maybe it's simulations all the way up?