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Warm Winter Vegetable Salad With Halloumi

['5 Tbsp. extra-virgin olive oil, divided', '2 garlic cloves, finely chopped', '1½ tsp. kosher salt', '1 tsp. Aleppo-style pepper', '½ small head of red cabbage (about 10 oz.), cut into 1" pieces', '1 medium red onion, cut into 8 wedges through root end', '1½ lb. winter squash, preferably delicata, halved, seeds removed, sliced crosswise ½" thick', '1 large pita bread, split into 2 layers, cut or torn into 1½"–2" pieces', '8 oz. Halloumi cheese, cut into 1" pieces', '2 Tbsp. apple cider vinegar', '1½ tsp. ground sumac', 'Mint springs (for serving)']

Preheat oven to 425°F. Coat a rimmed baking sheet with 1 Tbsp. oil. Mix garlic, salt, Aleppo-style pepper, and 3 Tbsp. oil in a large bowl. Add cabbage, onion, and squash and toss to coat. Spread out on prepared baking sheet (keep bowl handy) and roast until squash is browned underneath, 25–30 minutes.
Toss pita, Halloumi, and remaining 1 Tbsp. oil in reserved bowl. Scatter over vegetables, then turn vegetables over with a large spatula. Roast until squash is fork-tender and cabbage, onion, pita, and Halloumi are browned in spots (cheese should be soft inside), 15–20 minutes. Remove from oven and drizzle with vinegar. Top with sumac and mint.

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