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Preheat oven to 375°F. Lightly coat four 6-ounce custard cups or ramekins with cooking spray; set aside. Unfold phyllo dough; keep covered with plastic wrap, removing sheets as you need them. Lay one sheet of phyllo dough on a flat surface; lightly coat with cooking spray. Top with a second sheet; lightly coat with cooking spray. Using a sharp knife or pizza cutter, cut the phyllo stack lengthwise into two 14-inch-long strips. Cut each strip crosswise into two rectangles, making four total rectangles. Repeat with the remaining phyllo sheets and cooking spray to make four more rectangles.
Gently press one phyllo rectangle into one of the prepared custard cups, pressing the dough into the side of the cup. Place another rectangle crosswise over the first rectangle, pressing it into the side of the cup. Repeat with the remaining phyllo rectangles and custard cups. Set aside.
In a medium bowl, whisk together eggs, granulated sugar, milk, vanilla and salt. Whisk in sour cream until the mixture is smooth. Add flour, whisking until smooth.
Divide the batter among the phyllo-lined custard cups. Place a plum half, cut-side up, in the center of each custard cup.
Bake 20 to 25 minutes or until puffed and just starting to brown and the batter around the plum is set. Cool on a wire rack for about 15 minutes before serving. If desired, sprinkle with confectioners’ sugar; serve warm.