Roasted Tomato Basil Soup With Sausage Pesto Phyllo Cups

Everyone has their favorite soup, the one they turn to when they are sick or feeling bad, it’s cold outside, or that certain craving kicks in…well, mine is not tomato.  In fact, I didn’t even really like tomato soup for most of my life which is strange because I am a huge fan of tomatoes, like could eat a tomato like an apple fan.  But for some reason, I never developed that taste for warm, tomato flavor usually seasoned with basil until I tried it one day with grilled cheese and the flavors melded together so well those feel good taste buds on my tongue couldn’t help but respond.

I’ve learned to appreciate different kinds of soup depending on different conditions.  When I want a really hearty soup that will for sure fill me up I usually turn to clam chowder, when I want a lighter soup I turn to split pea, and now, with grilled cheese I turn to tomato.  The particular day that I chose to tackle tomato soup for the first time I knew I would not be satisfied with canned soup, nope, it had to be homemade with roasted tomatoes and appropriate amounts of basil to create the perfect combination.  Instead of making grilled cheese to compliment this soup however, I scavenged the fridge and found phyllo dough, sausage, and pesto and decided to tackle phyllo cups.  Let me tell you, phyllo dough is NOT my favorite thing to work with by far.  It keeps best when frozen but then you have to wait for it to thaw otherwise it just flakes apart.  However, I was determined to create this phyllo cup addition to the meal so I kept going with it.

Once you get past the annoying breakage of the phyllo dough it is actually quite simple and any combination of filling works well.  This particular filling ended up being pretty salty but was balanced well with the soup (and my salt loving sister devoured them).

Roasted Tomato Basil Soup


  • 3 pounds ripe plum tomatoes, cut in half lengthwise
  • 1/4 cup plus 2 tablespoons good olive oil
  • 1 tablespoon salt
  • 1 1/2 teaspoons freshly ground black pepper
  • 2 cups chopped yellow onions
  • 6 garlic cloves, minced
  • 2 tablespoons unsalted butter
  • 1/4 teaspoon crushed red pepper flakes
  • 1 (28-ounce) canned plum tomatoes, with their juice
  • 4 cups fresh basil leaves, packed
  • 1 teaspoon fresh or dried thyme leaves
  • 1 quart chicken stock or water


  1. Preheat the oven to 400 degrees F. Toss together the tomatoes, 1/4 cup olive oil, salt, and pepper. Spread the tomatoes in 1 layer on a baking sheet and roast for 45 minutes.
  2. In an 8-quart stockpot over medium heat, saute the onions and garlic with 2 tablespoons of olive oil, the butter, and red pepper flakes for 10 minutes, until the onions start to brown.
  3. Add the canned tomatoes, basil, thyme, and chicken stock. Add the oven-roasted tomatoes, including the liquid on the baking sheet. Bring to a boil and simmer uncovered for 40 minutes.
  4. Place contents in a food processor or blender and pulse until desired consistency.  Taste for seasonings.
  5. top with cheese if desired

Phyllo Cups with Sausage, Pesto, and Feta


  • Phyllo dough cut into 27 squares
  • 1/4 cup pesto
  • 3 tbl feta cheese crumbled
  • 2 sausage (whatever sausage you have or want to add, spicy or not)
  • olive oil
  • sundried tomato cream cheese to top (optional)


  1. Preheat oven to 400 degrees
  2. Coat the 9 muffin tin with cooking spray
  3. layer 3 phyllo squares at a time, brushing olive oil in between so they stick.  Place each set of 3 in each muffin hole
  4. in a separate bowl combine pesto, sausage (cut into bite size pieces), and feta
  5. add pesto mixture to fill each muffin cup about 1/2 full
  6. cook phyllo cups about 12 minutes or until edges of dough start to brown
  7. top with cream cheese if desire, ENJOY!


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