To make the sauce:
Heat the oven to 450°F. In a nonreactive roasting pan (not aluminum), combine the tomatoes, onions, crushed garlic, jalapeños, and oregano. Add the olive oil, salt, and pepper, and toss. Roast, stirring occasionally, until the onions and tomatoes are soft and slightly charred, about 1-1/2 hours.
Let the mixture cool and then pass it through a food mill fitted with a medium blade (or else through a medium-meshed sieve) to remove the seeds and cores. The sauce may be slightly chunky. If you want it smoother, purée it in a blender or food processor. Taste for salt and set aside.
To make the filling:
Boil about 4 cups salted water in a pot, add the broccoli raab, and parboil for 2 to 3 minutes. Drain, but reserve 1/4 cup of the cooking water. Chop the broccoli raab into very small pieces.
Heat the olive oil on medium high in a heavy-based frying pan. Add the sausage, breaking it up with a spoon into very small pieces. Add the garlic, red chile flakes, broccoli raab, salt, and pepper. Add the 1/4 cup of reserved broccoli raab cooking liquid and simmer until the sausage is cooked and the broccoli raab is tender, about 4 minutes. There should be no more than 2 Tbs. liquid left in the pan. Transfer to a bowl and let cool. The cooled mixture should be moist but not wet, so if there’s excess liquid in the bowl, drain it off. Mix in the 1-1/4 oz. Pecorino and the diced mozzarella.
To roll out and stuff the pasta dough:
Divide the ravioli dough into four equal pieces. Wrap three in plastic and return to the refrigerator. Flatten the fourth piece of dough with your hand (flour it lightly if necessary), and run it through the widest setting on your pasta machine twice. Set the rollers to the next narrower setting. Pass the dough through twice. Continue notching down by one setting and passing the dough through two times (the first pass roughs up the dough; the second pass smooths it out).
As the dough lengthens and thins, it will bunch up under the machine. Rectify this by gently lifting it out and folding it neatly behind the machine. When you can just see the shape and shadow of your hand through the dough sheet (it should be about 1/32 inch thick), stop rolling. You may not need to go to the narrowest setting
Cut the sheet in half crosswise and trim the sides to make two neat rectangles, one slightly larger than the other. On the smaller sheet, spoon mounds of 1 to 2 tsp. of the filling, leaving 1/2 to 3/4 inch between each mound. (For smaller ravioli, use less filling in each mound and space them more closely; for larger ravioli, use more.) Brush a little beaten egg yolk on the dough around each mound of filling.
Lay the second sheet of dough on top, draping it gently over the mounds without stretching it. Starting at one edge, gently press around the filling to push out any air pockets and seal the sheets.
Cut the pasta in between the mounds to form individual squares or circles with a scalloped pastry wheel or a ravioli stamp (if you don’t have either of these, try a biscuit cutter or a paring knife). Press on the mounds a bit to slightly flatten them and on the edges to confirm the seal. Roll out, fill, and cut any remaining dough the same way.
When ready to serve, bring a pot of salted water to a boil. Gently slide the chilled or frozen ravioli into the water and cook until they float and are tender, 3 to 5 minutes. Meanwhile, reheat the roasted tomato sauce. Taste for salt and pepper. If the sauce is too thick, add a little water from the pasta pot.
Drain the ravioli and toss with the sauce. Spoon onto a large serving platter or individual plates, sprinkle with Pecorino, and serve.
Make Ahead Tips
The roasted tomato sauce can be made several days ahead, and the filling can be made a day ahead. Uncooked ravioli can be refrigerated for up to a day or frozen, wrapped, for up to a month. If you're not cooking them right away, transfer the filled ravioli to a pan lined with waxed paper and sprinkled with semolina flour or cornmeal (don’t let them touch).
nutrition information (per serving):
Photo: Scott Phillips