He’s 2. He’s ready to get up 5:30, so be the adult and get up instead of making him sit for an hour by himself. I would cry too. You can try adjusting his wake times, but it sounds like you may need to adjust your bedtime so you’re ready to be up with him at 5:30 for now. When our kids were 2 they weren’t in cribs anymore, and would just come climb in our bed and fall back to sleep, or pester us until one of us got up.