Tiramisu Bomboloni

Getting reviews...
  • Level: Intermediate
  • Total: 3 hr 10 min
  • Active: 1 hr 40 min
  • Yield: about 32 bomboloni


For the Dough:

For the Filling:

For the Glaze:


  1. Make the dough: Warm the milk in a small saucepan over low heat until 105 degrees F to 115 degrees F. Transfer to a small bowl; stir in the yeast and granulated sugar. Set aside until foamy, 7 to 10 minutes. Meanwhile, whisk the flour and salt in the bowl of a stand mixer.
  2. Add the yeast mixture, eggs and vanilla to the stand mixer. Mix on medium speed with the dough hook until a shaggy ball of dough forms, 1 to 2 minutes. Mix in the butter, 1 piece at a time. Continue to knead the dough with the mixer, scraping the sides and bottom of the bowl occasionally with a rubber spatula, until smooth and elastic, about 6 minutes. Lightly coat a large bowl with cooking spray and transfer the dough to the bowl, turning to coat. Cover tightly with plastic wrap and let rise in a warm place until doubled in size, about 1 hour.
  3. Make the filling: Combine 3/4 cup milk, the granulated sugar, espresso powder and salt in a small saucepan and cook over medium heat, stirring, until the sugar dissolves and the milk is steaming. Whisk the remaining 1/4 cup milk with the egg yolks and cornstarch in a medium bowl. Gradually whisk the warm milk mixture into the egg mixture, then pour the mixture into the saucepan. Bring to a simmer, whisking constantly, until very thick, about 3 minutes. Strain the custard through a fine-mesh sieve into a bowl, pushing it through with a rubber spatula. Stir in the butter and vanilla until smooth. Place a piece of plastic wrap directly on the surface of the custard and refrigerate 30 minutes.
  4. Put the mascarpone in a medium bowl. Whisk in the chilled custard, one large spoonful at a time, until smooth. Transfer to a piping bag fitted with a 1/4-inch round tip. Refrigerate until ready to use.
  5. Lightly flour 2 baking sheets. Turn out the dough onto a lightly floured surface and gently pat until 1/2 inch thick. Cut out about 32 rounds using a 1 1/2-inch cutter; arrange 1 inch apart on the prepared baking sheets and lightly coat the tops with cooking spray. Cover with plastic wrap and let rise until puffy, about 1 hour.
  6. Heat 2 inches of vegetable oil in a large pot over medium heat until a deep-fry thermometer registers 340 degrees F. Meanwhile, make the glaze: Whisk the confectioners' sugar, Marsala and a pinch of salt in a medium bowl, thinning with more Marsala as needed. Cover and set aside.
  7. Working in batches, fry the bomboloni 30 seconds, then flip and continue frying, flipping occasionally, until browned, about 2 more minutes. Remove with a slotted spoon to a paper towel-lined baking sheet to drain. Let cool.
  8. Insert a chopstick or skewer into the side of each bomboloni and wiggle to form a small pocket. Pipe in the filling and dust the tops with cocoa powder. Drizzle with the glaze.