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Prep 1hr10min
Total5hr40min
Ingredients9
Servings42
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Ingredients
Cookies
1
cup butter, softened
1 1/2
cups packed brown sugar
1
teaspoon vanilla
3
eggs
3 1/2
cups all-purpose flour
1
teaspoon baking soda
Filling
1 3/4
cups chopped dates (from 8-oz bag)
3/4
cup granulated sugar
3/4
cup water
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Steps
1
In large bowl, beat softened butter and brown sugar with electric mixer on medium speed until light and fluffy, scraping bowl occasionally. Beat in vanilla and eggs until well blended. On low speed, beat in flour and baking soda until well combined, scraping bowl occasionally. Dough will be soft. Divide dough into 4 pieces; flatten each piece, and wrap in plastic wrap. Refrigerate about 3 hours or until dough is firm and cold.
2
Meanwhile, in 2-quart saucepan, mix Filling ingredients. Heat to boiling; boil 1 minute, stirring constantly. Reduce heat to low; simmer about 10 minutes, stirring occasionally, until mixture is darkened in color and thickens slightly. Pour filling mixture into small bowl; refrigerate uncovered until ready to use (mixture will thicken as it cools).
3
Heat oven to 375°F. Remove 1 piece of chilled dough from refrigerator, and unwrap. On work surface generously sprinkled with flour, roll out dough with floured rolling pin to 1/8 inch thick. Using floured 2 1/2-inch round cutter, cut out rounds. In half of the rounds, cut out and remove 1-inch round or desired shape of hole from center. Place whole rounds on ungreased cookie sheet.
4
Spoon 1 generous teaspoonful cooled filling onto center of each round; top with cut out dough round. With fingertips or floured fork, press edges of dough to seal. Return dough centers and leftover dough to refrigerator for rerolling.
5
Bake 7 to 9 minutes or until light golden brown. Cool 1 minute; remove from cookie sheet to cooling rack.
6
Meanwhile, repeat steps on assembling and baking with each portion of refrigerated dough, refrigerated leftover dough and remaining filling.
7
Cool cookies completely, about 1 hour. Store covered in airtight container.
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For best results and easy prep, use prepackaged chopped dates for the filling.
To help get cutout cookies off the surface to the cookie sheet, lightly press back of the cookie spatula in flour and slide under cookie dough for easy lifting.
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