Grape-Filled Cookies (The 5th Sweet of Christmas)

Are you ready for possibly the most challenging cookie ever?  This is my Everest.  This is my Waterloo.  This is my "coconut cream pie of cookies."  (I'll get to that reference in a later post.)

But, if you take the challenge and are willing to deal with the possibility of crazy gooey oozy grape mess on your cookie sheets, you'll be delighted with the final result.  I promise.


Grape-Filled Cookies
Ingredients


Filling

• 12 ounces of grape jelly
• 8 ounces mini semi-sweet chocolate chips
• 1 cup chopped walnuts
• 1 teaspoon cinnamon
• 1 tablespoon orange marmalade
• 2 tablespoons flour

Cookie

• 5 cups flour
• 1 and 1/2 cups sugar
• 3 teaspoons baking powder
• 1/2 cup shortening
• 1 teaspoon vanilla
• 4 eggs
• 1/2 cup milk
• confectioners sugar

Method:

1. In a medium bowl, mix all filling ingredients well and chill while you make the cookie dough.  The filling must be fairly stiff and not runny.
2. In a large bowl, mix cookie ingredients by hand (you can use a pastry cutter to get it started but it works best if you roll up your sleeves and get your hands into it - literally).  The dough should be stiff.
3. Roll into eight small balls.
4. Roll out onto floured surface to a small rectangle at a 1/4 inch thickness.
5. Spoon filling into the center, do not overfill.  You will likely have extra filling leftover.
6. Fold long edges over filling, then fold short edges over filling, overlapping, to make a little patty.
7. Place sealed side down on a parchment lined cookie sheet.
8. Bake at 350 degrees for 15 minutes.
9. Coat top immediately with confectioner's sugar and let cool completely.
10. Cut into strips, then pack in confectioner's sugar into airtight containers, with wax paper between layers, and freeze to set cookies.

Notes:

• I don't normally recommend specific brands - everyone has their own preferences.  But after years of experience, as my mother's "apprentice" and on my own, I've found that you really need to use Smucker's jelly.  It's much, much thicker than any other brand I've ever used and I think that's the key to filling that doesn't run out of the cookie while baking.
• The first few times you make these cookies, you'll roll the dough too thin or over fill the patties, and they'll crack and ooze filling all over your cookie sheet.  This is okay, I promise. It does take practice to get it right.
• Freezing the cookies is imperative.  The filling won't set properly if they aren't frozen. To serve, just break the strips apart and allow them to come to room temperature.  You can also cut the strips in half or thirds and put them in little paper cups to serve.