Brandy Old-Fashioned Thumbprints

Name: Brandy Old-Fashioned Thumbprints
Prep time: 30 min
Cook time: 15 min
Total time: 45 min
Yield: about 3 dozen
Ingredients: 1 cup butter, softened; 1-1/4 cups confectioners' sugar; 2 teaspoons grated orange zest; 1 teaspoon salt; 1/2 cup orange juice; 2-1/2 cups all-purpose flour; CHERRY FILLING:; 1 cup red tart cherry fruit spread; 1 cup finely chopped brandied cocktail cherries; 2 tablespoons brandy; 1/2 teaspoon bitters; Pinch of salt; ORANGE BRANDY GLAZE:; 1 cup confectioners' sugar; 3 teaspoons orange juice; 2-1/2 teaspoons brandy; 2-3 dashes bitters; 1/2 teaspoon grated orange zest; Pinch of salt; Grated orange zest, for garnish, optional

TEST KITCHEN APPROVED

Total Time:Prep: 30 min. + chilling Bake: 15 min./batch

By Taste Of Home Editorial Team

Recipe by Sarah Farmer, Waukesha, Wisconsin

Tested by Taste of Home Test Kitchen

Taste of Home's Editorial Process

Published on Aug. 07, 2026

These thumbprint cookies taste just like a classic Wisconsin brandy old-fashioned cocktail. The shortbread cookie bursts at the seams with orange flavor, while the brandied cherry filling brings the boozy flavor. Serve them alongside a cocktail for a perfect after-dinner treat. —Sarah Farmer, Waukesha, Wisconsin

TEST KITCHEN APPROVED

Brandy Old-Fashioned Thumbprints

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Yield:about 3 dozen

Prep:30 min

Cook:15 min

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Ingredients

1 cup butter, softened
1-1/4 cups confectioners' sugar
2 teaspoons grated orange zest
1 teaspoon salt
1/2 cup orange juice
2-1/2 cups all-purpose flour
cherry filling:

1 cup red tart cherry fruit spread
1 cup finely chopped brandied cocktail cherries
2 tablespoons brandy
1/2 teaspoon bitters
Pinch of salt

orange brandy glaze:

1 cup confectioners' sugar
3 teaspoons orange juice
2-1/2 teaspoons brandy
2-3 dashes bitters
1/2 teaspoon grated orange zest
Pinch of salt
Grated orange zest, for garnish, optional

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Directions

1
Preheat oven to 350°. In a large bowl, cream first 4 ingredients until light and fluffy, 3-4 minutes. Add flour to creamed mixture alternately with orange juice, beating well after each addition.

2
Fit a pastry bag with a large open star tip. Transfer dough to prepared bag; pipe 1-in. stars 2 in. apart onto parchment-lined baking sheets. Using the back of a rounded teaspoon measure, make an indentation in the center of each cookie. Refrigerate for at least 2 hours.
3
Meanwhile, in a medium bowl, combine all filling ingredients; set aside.
4
Bake cookies until bottoms are light brown, 12-13 minutes. Cool on pan 5 minutes before removing to wire racks to cool.
5
For glaze, in a small bowl, combine all ingredients. Drizzle over cookies. Sprinkle with additional orange zest, if desired.