Savory Tomato-Topped Italian Herb Rolls

Gaaaa! My tomatoes are multiplying in my garden. And, thus, I’m on the hunt for tomato recipes galore. I was looking for a bread made with fresh tomatoes (there is such a thing!) when I stumbled upon this delicious looking recipe for a bread dish made with fresh tomatoes at the website simmer till done. Please visit Marilyn’s website – specifically her Upside-Down Tomato Basil Bread recipe – and try to tell me that you wouldn’t have wanted to try the recipe immediately after seeing it. Then check out my adaptation below.

These rolls remind me of a savory cinnamon roll. (Replace the cinnamon with herbs and the glaze with cheese.) Both my dad and I ate two right out of the pan. I would have eaten three but I didn’t want to be obtusely full.

This is a fantastic and impressive appetizer or side dish. I used tons of herbs to boost the flavor. The pinches of red chili flakes gives it a little bit of a kick. If you’re looking to wow someone, replace the rolls or breadsticks that normally accompany your favorite Italian dish with these cheesy herbed rolls. You won’t be sorry! I should give you fair warning, these rolls although not overly complicated, take a long time to make.

dough ingredients.

  • 2 ½ tsp. (1 package) active dry yeast
  • 1 c. plus 3 T. warm water
  • 4 T. plus 1 tsp. olive oil
  • 3 ¾ c. unbleached all-purpose flour
  • ½ c. shredded Asiago Cheese
  • 1 T. dried rosemary (ground)
  • 1 tsp. dried oregano
  • 1 tsp. dried sage
  • 1 tsp. dried thyme
  • 1 tsp. dried parsley
  • 2 tsp. sea salt
  • 1 tsp. coarsely ground black pepper
  • 2 dashes of crushed red pepper flakes (optional)
  • cornmeal, for sprinkling

dough directions.

  1. In the bowl of a stand mixer, stir the yeast into warm water (about 100 to 110 degrees F) and let stand about 10 minutes, until yeast looks bubbled and creamy. Fit mixer with dough hook. Stir in olive oil and combine with yeast. Mix in flour, Parmesan cheese, sea salt, ground black pepper, herbs and hot pepper flakes. Start mixing on low and increase to medium speed, kneading about 5 minutes, until dough is combined, soft and elastic.
  2. If dough looks too dry: add a little more olive oil while mixer kneads the dough until dough just combines. If dough looks too wet: add small amounts of flour while mixer kneads the dough, until sides of bowl look clean and dough combines.
  3. Place the dough in lightly oiled bowl; cover loosely with plastic wrap and set aside to rise until doubled. The dough should feel smooth, moist and soft.
  4. When the dough is almost risen, make the filling & tomato topping.

filling ingredients.

  • 4 to 5 T. fresh basil, finely chopped
  • 2 c. shredded Parmesan cheese
  • ½ c. olive oil
  • 1 tsp. sea salt
  • 1 tsp. coarsely ground black pepper
  • 2 pinches crushed red pepper flakes (optional)

filling directions.

In a bowl, place chopped fresh basil, Parmesan cheese, olive oil, sea salt, ground pepper and red pepper flakes (if using). Stir to combine well, and set aside.

tomato topping ingredients.

  • 3 large or 4 small-medium tomatoes
  • ¼ c. red onions, roughly chopped
  • basil leaves, torn
  • sea salt, sugar, crushed red pepper flakes (optional)
  • Asiago or Parmesan cheese, shredded (optional)

tomato topping directions.

  1. Remove tomato cores, seeds and juice. Chop remaining tomato meat into rough bite-size pieces. Place in bowl and pat down with paper towel to dry off.
  2. Stir in red onions and pieces of torn basil and set aside.

assembly directions.

  1. Lightly oil (with olive oil) bottom and sides of 9″ round cake or springform pan. Spread chopped tomato mixture evenly over bottom of pan. Set aside.
  2. Turn risen bread dough out on lightly floured surface. Gently pull and stretch dough (or use a rolling-pin) to form dough into a rough rectangle, approximately 1′ x 2′. Spread filling evenly across dough to cover – all the way to the edges. If you feel like you don’t have enough filling, sprinkle some more cheese in the bare spots.
  3. Starting at the long edge and roll dough jelly-roll style (like you would with cinnamon rolls) Try to roll as evenly as possible. With seam side facing down, pat sides and edges to seal.
  4. Using a serrated sharp knife cut 1 1/2 to 2″ slices from dough roll. Arrange slices, spiral side down, on top of the chopped tomato mixture in prepared pan. Cover lightly with plastic wrap and allow to rise slightly, about 20 minutes, while you preheat your oven to 400 degrees F.
  5. Place the pan on or above a baking sheet with edges to catch drips. Bake on lower rack 40 to 45 minutes, until top rolls are medium brown, feel hollow when tapped, and tomato juices have bubbled and thickened. Remove from oven and cool on rack for 5 minutes.
  6. Have a platter or plate ready to unmold. Loosen around the edges of the pan with a knife. Cover the browned top of rolls with your platter or plate. The pan will still be warm so use oven mitts. Holding the platter and pan together, turn over in one motion until pan is upside down. Carefully lift pan from bread, releasing steam slowly. Lift pan off completely, revealing tomato-topped bread.
  7. Turn the bread out onto a baking sheet. Preheat the broiler. Mix together optional sea salt, sugar and red pepper flakes. Sprinkle salt mixture over tomato topping. Cover with additional shredded cheese. Place under broiler for 1 to 2 minutes, watching carefully, until tomatoes sizzle and edges blacken. Remove and serve.

Recipe rating: 


  1. Your herb rolls are very interesting and they look very tasty. I would love to eat them with some soup or better still just chomp on them, as a snack. Thanks for sharing this recipe. I have bookmarked it for my next soup. I love eating soup. Have a wonderful weekend ahead!


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