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powdered sugar chocolate sandwich cookies with a strawberry jam filling
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Jam Filled Chocolate Sandwich Cookies
Prep Time
1 hr 20 mins
Cook Time
10 mins
Total Time
1 hr 30 mins
 
Jam Filled Chocolate Sandwich Cookies begin with a fudgy chocolate sugar cookie dough cut out into stars and end with an orange strawberry jam in the middle. One of my favorite chocolate cookie sandwiches, and it makes a stunning holiday cookie recipe!
Course: Dessert
Cuisine: American
Keyword: jam filled chocolate sandwich cookies
Servings: 18 sandwich cookies
Author: Michelle
Ingredients
Chocolate Cookies
  • 1 cup unsalted butter, softened
  • 1 1/2 cups unsweetened cocoa powder
  • 1 1/4 cups granulated sugar
  • 1/2 tsp baking powder
  • 3/4 tsp salt
  • 1 tsp espresso powder
  • 4 oz semi-sweet chocolate, melted and cooled
  • 2 eggs
  • 1-2 Tbsp milk (whole milk or 2% is best)
  • 1 tsp vanilla extract
  • 1 1/2 cups all purpose flour
Jam:
  • 2/3 - 1 cup strawberry jam
  • 2 tsp orange zest (optional)
  • 1 Tbsp orange juice, fresh (optional)
Tools:
  • 1 large star cookie cutter
  • 1 small star cookie cutter
  • or, you can use circle cookie cutters, hearts, etc.
Instructions
  1. With a hand mixer or a standing mixer, beat unsalted butter until light and fluffy, about 1 minute.
  2. Add in cocoa powder, granulated sugar, baking powder, salt, and espresso powder. Mix until combined.
  3. Next, add in melted and cooled chocolate; mix until combined.
  4. Then, add in the eggs, one at a time, beating well after each addition.
  5. Add in vanilla extract and 1 Tbsp of milk.
  6. Lastly, add in the flour and mix until the flour is completely incorporated. If the dough is too dry (it’s crumbly and not sticking together), add in the remaining Tbsp of milk.
  7. Chill the dough for 1 hour, at least.
  8. Once the dough is chilled, preheat the oven to 375 degrees and line a baking sheet with parchment paper (or spray with baking spray).
  9. On a floured surface (alternatively, you could use cocoa powder or powdered sugar), roll dough out to 1/4” thick.
  10. (The dough will make about 36-40 cutout star cookies, thus making about 18-20 sandwich cookies.)
  11. Cut out large star shapes with your cookie cutter, and place the about 2” apart on the cookie tray.
  12. Using the small star cookie cutter, cut out the centers of half of the unbaked cookies (these will be the tops of the cookie sandwiches).
  13. Bake for 9-10 minutes, or until the edges are just firm, and the centers of the cookies are just set (this ensures they will be very soft).
  14. Allow to cool on the tray for a few minutes, then transfer to a cooling rack.
  15. While the cookies are cooling, mix strawberry jam, orange zest, and orange juice in a small saucepan. Cook on med-low heat for 3-4 minutes, until jam is warm and orange juice is completely mixed in. Let the jam cool to room temperature.
  16. Spoon about 2 tsp of jam onto the centers of the bottom sandwich cookie, spreading the jam out from the centers a little bit. Top with the top sandwich cookies (the ones with the small star cutout).
  17. Dust with powdered sugar, if desired.
  18. Store at room temperature or in the fridge (I actually loved these out of the fridge! The cookie is extra rich and fudgy out of the fridge).
  19. Enjoy!
Recipe Notes

*You can omit the orange juice and orange zest, if desired. I would still warm up the jam to thin it out before adding to the cookies.
*Depending upon how much jam you like in your cookies, use anywhere from 2/3 - 1 cup of jam.