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Wash and dry the cabbage, remove only the outer wrapper leaves, and slightly trim the stem, leaving the core intact. Cut the cabbage lengthwise into quarters.
Place the cabbage quarters in the skillet, generously coat all sides with olive oil using a silicone brush, and sprinkle evenly with salt and pepper. Cover the skillet tightly with a lid and roast for 40 minutes.
Remove the skillet from the oven, uncover, and gently flip each cabbage quarter so one cut side is facing down. Roast uncovered for 15 minutes, then remove and flip again so the other cut side is facing down. Continue roasting for 10-15 minutes, watching closely to prevent burning.
Insert a knife into the thickest part near the core—it should slide in and out effortlessly. If there’s resistance, return to the oven uncovered for 10 more minutes until the cabbage is soft and tender throughout, with no crunchy areas. Serve immediately with tahini sauce drizzled on top or on the side.
Once fully cooled to room temperature, store leftovers in an airtight container in the refrigerator for up to 5 days. To reheat, place in a lightly oiled cast iron skillet at 400°F for 10 minutes or until warmed through. Store the sauce separately.