Prepare baking dish: Grease a 9-inch round baking dish or cast iron skillet.
Shape dough: On a lightly floured surface, gently stretch or roll out the sourdough dough into a large circle, about 12-14 inches in diameter.
Add filling: Sprinkle half of the brie cubes evenly over the dough. Scatter half of the cranberries over the brie. Fold the dough in half, then in half again, creating a layered semicircle. Gently press the layers together.
Cut and arrange: Cut the dough into 1-inch wide strips, starting from the folded edge and leaving about 1 inch uncut at the other end. Twist each strip a few times and arrange them in the prepared baking dish, starting from the outside and working your way inwards. It’s okay if the strips overlap.
Add remaining filling: Sprinkle the remaining brie cubes and cranberries over the arranged dough.
Drizzle and season: Drizzle the olive oil evenly over the bread. Sprinkle with thyme leaves, sea salt, and black pepper.
Bake: Cover the baking dish loosely with plastic wrap and let the dough rise in a warm place for 30-45 minutes, or until it has puffed up slightly. Remove the plastic wrap. Bake at 375°F (190°C) for 30-35 minutes, or until the bread is golden brown and the brie is melted and bubbly.
Cool and serve: Let the bread cool slightly before serving. Drizzle with honey or maple syrup, if desired. Pull apart and enjoy!