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Gather the ingredients. Heat the oven to 425 F (220 C/Gas 7). Brush a large rimmed baking sheet with olive oil or line the pan with foil and brush the foil. Rinse the okra and pat dry with paper towels. Trim the pods, discarding the stem ends and tips. Slice the okra pods into 1/2-inch rounds and put them in a large bowl. Slice the grape tomatoes in half (lengthwise or crosswise) or slice in 3 or 4 pieces if they are large. Put the sliced tomatoes in the bowl with the okra. Drizzle the olive oil over the okra and tomato mixture and then season with the salt and pepper. Toss to coat well. Arrange the seasoned okra and tomatoes in a single layer in the prepared baking pan. Bake the vegetables for 15 to 20 minutes, or until lightly browned around the edges, turning occasionally.