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Step 1
Preheat the oven to 350°F and set a rack in the center. Cut off the top ½-inch of each garlic head and add cut-side up to a 10-inch cast iron skillet. Add the herbs, peppercorns, and chile and pour the olive oil on top of the heads.
Step 2
Cover the skillet tightly with foil and roast until the garlic is soft, about 45–50 minutes. Raise the tempature to 400°F, remove the foil, and continue baking until the tops are browned, about 5 minutes more.
Step 3
Remove the skillet from the oven and cool enough to handle easily. Separate the cloves and squeeze the pulp into a large heatproof jar. Discard the skin and herbs. Strain the oil over the cloves. Add additional oil to ensure the cloves are fully covered. Use immediately or refrigerate for up to 2 weeks.