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–+ servings
Prune-Raisin Filled Cookies
These Prune-Raisin Filled Cookies are a rich, nostalgic treat made from a tender dough wrapped around a sweet, spiced fruit and nut filling. With deep roots in mid-century American baking, they offer a soft, chewy bite balanced by the bold flavor of cooked prunes and raisins. While they may not be widely known today, they were once a cherished part of holiday spreads and community cookbooks. This version includes notes suggesting alternate fillings like dates or oats, showing how flexible and beloved the base recipe has remained over time.
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Prep Time 40 minutes
Cook Time 20 minutes
Total Time 1 hour
Course Snack
Cuisine American
Servings 36 cookies
Calories 165 kcal

Ingredients
  

Dough

  • 3 cups all-purpose flour
  • 1 cup granulated sugar
  • 1 tsp baking soda
  • ½ tsp salt
  • 1½ cups shortening
  • 3 tbsp milk
  • 2 eggs (large)
  • 1 tsp cream of tartar
  • 1 tsp vanilla extract

Filling (double if desired)

  • 2 tsp all-purpose flour
  • ½ cup granulated sugar
  • ½ cup raisins
  • ½ cup prunes (cooked, or dates as a variation)
  • ½ cup nuts (chopped, e.g., walnuts or pecans)

Instructions
 

Step 1: Prepare Dry Ingredients

  • Sift together flour, sugar, baking soda, and salt into a large bowl.

Step 2: Incorporate Shortening

  • Cut shortening into the sifted dry ingredients until crumbly.

Step 3: Mix Wet Ingredients Separately

  • In a separate bowl, beat milk, eggs, cream of tartar, and vanilla.

Step 4: Combine and Chill

  • Add the wet mixture to the dry mixture and combine well.
  • Cover and refrigerate overnight.

Step 5: Make Filling

  • Put raisins and prunes (or dates) through a food chopper or processor.
  • Combine with flour, sugar, and chopped nuts.
  • Mix well and set aside.

Step 6: Roll and Fill Dough

  • Roll dough on a floured surface to about ¼-inch thick.
  • Cut circles using a glass or cookie cutter.
  • Place 1 tsp of filling in the center of each circle.
  • Fold in half and seal the edges.

Step 7: Bake

  • Place cookies on a baking sheet.
  • Bake at 350°F for 10 to 20 minutes, watching closely to avoid burning.

Tips

  • Use dates instead of prunes for a milder, sweeter filling.
  • Add cinnamon or orange zest to the filling for extra depth.
  • Chill dough well to make rolling easier and prevent sticking.
  • For a softer texture, substitute half the shortening with butter.
  • Use a fork to crimp edges for a decorative look.
  • Swap in quick oats for nuts to make a nut-free version.

Nutrition

Calories: 165kcalCarbohydrates: 24gProtein: 2.5gFat: 7gSaturated Fat: 3gPolyunsaturated Fat: 1gMonounsaturated Fat: 2.5gCholesterol: 20mgSodium: 110mgPotassium: 185mgFiber: 2gSugar: 14gVitamin A: 140IUVitamin C: 1.2mgCalcium: 22mgIron: 0.9mg
Keyword filled cookies, heirloom recipe, holiday baking, old-fashioned cookies, prune filling, raisin cookies, vintage baking
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