Preheat oven to 425F.
Toss broccoli (if using) in salt, black pepper, and 1 tbsp olive oil.
Core and halve peppers lengthwise. Lay peppers and broccoli (if using) on two baking sheets, pressing the peppers down so they lay relatively flat.
Roast vegetables for 20-25 minutes, or until they have begun to brown.
Remove and set broccoli aside (it’s done). Slice roasted peppers into strips.
In a large bowl, combine sliced roasted peppers, spinach, goat cheese, garlic, oregano, basil, parsley, and remaining 1 tbsp olive oil. Mix with your hands until all ingredients are mixed and the spices have evenly distributed throughout the filling.
Slice each chicken breast from the side, taking care not to cut any in half, so that a “pocket” forms.
Add ¾-1 cup filling to each “pocket”, depending on the size of your chicken breasts.*
Wrap 3-4 strips of bacon tightly around each chicken breast, tucking the ends underneath. **
Lay each assembled chicken breast on a baking sheet. Sprinkle 1/8 tsp garlic powder and a pinch of salt onto each.
Bake at 425F for 15 minutes. Flip and bake for an additional 20 minutes.
If desired, flip again and broil on high for 3-4 minutes, or until the bacon begins to crisp. Serve with previously-roasted broccoli or your side of choice!