Preheat the oven to 350 degrees F and line a baking sheet with parchment paper or foil.

Using a serrated knife, carefully cut off the top quarter of the bread bowl. Place the wheel of brie in the center and use a sharp knife to trace around the wheel of brie. Remove the brie and carefully tear out the circle of bread, making sure not to tear through the bottom of the bowl.

Now, cut slices around the edge of the bread bowl about an inch and half, making sure not to cut all the way through to create your dipping pieces for later. Brush the bottom and inside of the bread with olive oil, then sprinkle with salt, pepper, and half of the thyme leaves. Place the brie in the middle and sprinkle with the remaining thyme leaves. Spoon the cranberry sauce over the top of the brie and then place the top of the bread over it.

Place the bread bowl on the prepared baking sheet and bake for 20 minutes.

Once done, gently remove the bread top (if any cranberry sauce sticks to it, gently scrape it off with a spoon back onto the top of the brie. Serve immediately.