Preheat oven to 350°F. Line a baking sheet with parchment paper.
Cut the top off the bread and carve out the inside so the wheel of brie will fit inside and the bread doesn’t come up more than ¼” above the cheese.
Slice into the bread at 1” intervals all the way around the circle so pieces can be pulled out easily.
Brush the inside of the bread with olive oil. Season with salt and pepper.
Cut the rind off the top of the brie and place the wheel in the bread bowl.
Sprinkle on the rosemary. Spoon the cranberry sauce over the brie.
Put the top of the bread bowl back on and set on the baking sheet. You can place the other pieces of bread taken from inside the bowl on the baking sheet as well.
Bake for about 20 minutes, until the cheese is fully melted.