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Pat cherries dry with paper towels; set aside. For filling, stir together cream cheese, powdered sugar and almond extract in a medium bowl. Fold in cherries and 2 ounces chocolate.
Preheat oven to 375°F. Line a baking sheet with parchment paper; set aside. Unroll phyllo dough; cover with plastic wrap. (As you work, keep the phyllo covered to prevent it from drying out; remove sheets as you need them.) Place one sheet of phyllo on a work surface; brush with some of the melted butter. Top with a second sheet of phyllo. Repeat brushing and layering four more times (six sheets total). Brush top with melted butter. Cut phyllo stack crosswise into thirds, then lengthwise in half to make six squares. Repeat with the remaining phyllo sheets and more melted butter to make 12 squares total.
Spoon 1 tablespoon of the filling near the bottom edge of each phyllo square. Fold bottom edge of phyllo over filling; fold in sides. Roll up to enclose filling, folding in sides as you roll. Place rolls, seam-sides down, on the prepared baking sheet. Brush tops with the remaining melted butter.
Bake for 15 to 17 minutes or until golden. Transfer to a wire rack; cool.
In a small saucepan, cook and stir the remaining 2 ounces chocolate and shortening over low heat until melted and smooth. Place strudel rolls on waxed paper. Drizzle with melted chocolate; let stand about 30 minutes or until chocolate is set.