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1. Preheat oven to 400 degrees F. Prepare Sweetened Pastry for Double-Crust Pie. On a lightly floured surface roll half of the dough at a time into a 12-inch circle. Using a 2 1/2-inch round or scalloped cookie cutter, cut dough into rounds; reroll scraps as necessary (you should have 40 rounds total). Place half of the pastry cutouts 2 inches apart on parchment- or foil-lined baking sheets, allowing space for sticks. Spread each round with some of the raspberry jam, leaving a 1/2 inch border. Press lollipop sticks gently into the pastry cutouts on the baking sheets, about 3/4 way atop the round.
2. Place pie filling in a medium bowl. Using kitchens scissors, snip fruit into small pieces. Stir in 1/4 teaspoon almond extract and cinnamon.
3. Spoon 1 teaspoon of the peach mixture onto the centers of the pastry cutouts on the baking sheets. Top each with a raspberry. Brush edges with milk. Top with the remaining pastry cutouts; seal edges with a fork. Brush with a little milk.
4. Bake for 14 to 16 minutes or until golden brown. Using a spatula, transfer pastry pops to wire racks (do not pick up by sticks while hot); cool completely.
5. For icing, in a small bowl whisk together powdered sugar, 2 teaspoons milk, and 1/8 teaspoon almond extract. Stir in additional milk, 1 teaspoon at a time, until icing reaches drizzling consistency. Drizzle icing over cooled cookies. If desired, sprinkle evenly with chopped almonds. Let stand until icing is set.
