Drizzle about 1 1/2 teaspoons olive oil into the bottom of each 6-ounce ramekin and sprinkle about 1 tablespoon basil per ramekin over the oil. Place 1 goat cheese piece over the basil in each ramekin; surround with sliced cherry tomatoes. Top with cracked black pepper and cayenne. Spread 1 1/2 teaspoon of the remaining basil on top of each portion, place ramekins on a baking sheet, and drizzle each serving with 1 1/2 teaspoons more olive oil.
Bake in the preheated oven until bubbling, about 15 minutes. Serve warm.
2 tablespoons olive oil, divided
3 tablespoons basil chiffonade (thinly sliced fresh basil leaves), divided
1 (4 ounce) log of fresh goat cheese, halved
16 cherry tomatoes, cut in half on the diagonal
freshly ground black pepper to taste
1 pinch cayenne pepper, or to taste