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Step 1
Heat the oven to 450°F with a rack in the middle position. In a colander set over a large bowl, toss the tomatoes with ½ teaspoon salt; set aside, tossing a few times to encourage the liquid to drain.
Step 2
On a rimmed baking sheet, combine the bread and fennel. Drizzle with 4 tablespoons oil and sprinkle with ¼ teaspoon each salt and pepper; toss to coat, then distribute in an even layer. Roast until the fennel begins to soften, about 10 minutes.
Step 3
Remove the baking sheet from the oven. Sprinkle the cheese over the bread mixture, then, using a wide metal spatula, scrape up and flip the mixture while mixing in the cheese. Redistribute in an even layer. Roast until the bread is browned and crisp and the fennel is tender and browned at the edges, another 10 to 15 minutes. Cool until barely warm, about 10 minutes.
Step 4
Discard the tomato juices in the bowl, then transfer the tomatoes to the bowl. Add the remaining 1 tablespoon oil, the vinegar, parsley and ½ teaspoon pepper; toss. Add the bread-fennel mixture and toss again. Taste and season with salt and pepper. Transfer to a serving dish and drizzle with additional oil.