Pie Filled Sugar Cookies

Another of my family’s favorite Christmas cookies. These filled sugar cookies–or Surprise Cookies, as my husband calls them–are soft, tender, and filled with various pie fillings. 

When I was little, my mom and grandma made these cookies every Christmas. And then when I was eight, I sneaked about a dozen of them and the next morning when I got off the school bus, I vomited cherries all over the sidewalk. My bus driver loaded me back on the bus, took me home, and Mom didn’t make the cookies again for 17 years.

I had completely forgotten that they existed! But then last year, Zach and I walked into her kitchen and there they were! I couldn’t believe it. Zach, who had never had them before, fell in love with them.

So now for Zach’s back story. When he was little, he was completely obsessed with Sesame Street. And in one of the books he had, there was a recipe for something called “Surprise Cookies.” He asked his mom to make them for years, but it never managed to happen. When he bit into one of my mom’s cookies, it reminded him of the ones he saw in that book. So he was thrilled.

These cookies are just as good as I remember them. And I weaseled the recipe out of my mom. 😛

Filled Sugar Cookies (a.k.a. Surprise Cookies)

For cookies:

• 1 cup of shortening (that is not a typo)
• 2 cups sugar
• 4 eggs
• 2 tsps vanilla extract
• 1 tsp salt
• 1/2 tsp baking soda
• 5 cups flour
• 1-2 tbsps water (if needed)
• pie fillings (I used cherry, blueberry, and strawberry–my mother uses pineapple, raisin, and cherry)
• milk
• sugar

For raisin filling:

• 2 cups brown sugar
• 3 cups water
• 4 cups raisins
• 6 tbsps cornstarch

Pineapple pie filling recipe

Step 01: Cream together the shortening and sugar until fluffy. Add eggs and vanilla, then salt and baking soda. Slowly add the flour. If dough is too crumbly, add 1-2 tablespoons of water, a little bit at a time (stop adding when you get the desired consistency–it should be easy to roll). Chill the dough for at least 1 hour.

Step 02: While the dough is chilling, make the raisin and pineapple fillings.

I actually don’t do this because I don’t like either one of those. But the pineapple is my dad’s favorite and raisin is mom’s, so she makes them…and I’m including these instructions for anyone else who likes pineapple and raisin. (My favorites pie fillings for these cookies are cherry and strawberry. My sister likes cherry and blackberry. We have tried blueberry and it’s pretty good, but not my favorite.)

Anyway.

For the raisin filling: Add all of the ingredients to a pot until thick. If you’re using other fillings, cut this recipe in half. This makes a lot of filling.

Some stores sell pineapple pie filling and some don’t. If you can find it in a store, it’s perfectly fine to use. For some reason, stores in my area are slowly getting rid of it…so this year I decided to make my own.

For the pineapple pie filling: In a pot, cook the crushed pineapple, cornstarch, sugar, and salt until thick. Add the butter and lemon juice. If using other fillings, cut recipe in half. And definitely do not double it. I don’t know what possessed me to do that, but I wound up with more pineapple pie filling than I could ever use.

Step 03: Once the dough has finished chilling, preheat your oven to 350°F. Flour your rolling pin (not too much, though, or it will make the dough difficult to work with) and roll out the dough on a prepared surface.

Cut the dough into 3-inch circles (a mason jar lid will work) and place the dough on a prepared baking sheet. Put a spoonful of pie filling on the circle. Roll the dough again, cut out more circles, and place those circles on top of the pie filling. Use a fork to press and seal the edges. Brush each cookie with milk and sprinkle with sugar.

 (Optional: use the large end of a turkey baster to cut little round holes into the top circle before placing it. That way, you can tell what each cookie is. Also, the filling won’t explode out of the sides when you seal them, because they’ll have some wiggle room in the center.)

Step 04: Bake for 12-15 minutes. Let cool on the cookie sheet for about 5 minutes and then move to a cooling rack.

These are delicious, though kind of a pain to make (hence why they are only made at Christmas).

A mason jar and a fork will serve you just fine while cutting out the cookies. However, Mom and I both use a Cut-N-Seal cookie cutter by Pampered Chef. It has made these cookies so much easier and faster to make. I highly recommend buying one if you’re going to make a lot of these. They’re also good for making hand pies and sandwiches for your kids lunches. (Note: I am not affiliated with The Pampered Chef and I won’t receive anything if you buy their product. I just really like the Cut-N-Seal.)

Enjoy!

UPDATE 12/19/13: I made another batch of these the other night and ran out of pie filling. So I substituted with blackberry jam and it was delicious. So if anyone is wondering if they can use jam on these, you most certainly can! I just globbed a tablespoon into the center and covered it with the cookie dough as normal. 🙂

UPDATE 11/28/14: I made a pumpkin filled version of these. Also amazing! I think the pumpkin are Zach’s favorite right now. 🙂

Pie Filled Sugar Cookies

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Prep Time: 1h 30m Cooking Time: 12-15m

Ingredients

• For cookies:

• 1 cup of shortening (that is not a typo)
• 2 cups sugar
• 4 eggs
• 2 tsps vanilla extract
• 1 tsp salt
• 1/2 tsp baking soda
• 5 cups flour
• 1-2 tbsps water (if needed)
• pie fillings (I used cherry, blueberry, and strawberry--my mother uses pineapple, raisin, and cherry)
• milk
• sugar

• For raisin filling:

• 2 cups brown sugar
• 3 cups water
• 4 cups raisins
• 6 tbsps cornstarch

• For pineapple filling:

• 3/4 cup white sugar
• 3 tbsps cornstarch
• 1 (20 oz) can crushed pineapple
• 1 tbsp lemon juice
• 2 tbsps milk
• 1 tbsp white sugar

Instructions

 

Step 01: Cream together the shortening and sugar until fluffy. Add eggs and vanilla, then salt and baking soda. Slowly add the flour. If dough is too crumbly, add 1-2 tablespoons of water, a little bit at a time (stop adding when you get the desired consistency–it should be easy to roll). Chill the dough for at least 1 hour.

Step 02: While the dough is chilling, make the raisin and pineapple fillings.

I actually don’t do this because I don’t like either one of those. But the pineapple is my dad’s favorite and raisin is mom’s, so she makes them…and I’m including these instructions for anyone else who likes pineapple and raisin. (My favorites pie fillings for these cookies are cherry and strawberry. My sister likes cherry and blackberry. We have tried blueberry and it’s pretty good, but not my favorite.)

Anyway.

For the raisin filling: Add all of the ingredients to a pot until thick. If you’re using other fillings, cut this recipe in half. This makes a lot of filling.

Some stores sell pineapple pie filling and some don’t. If you can find it in a store, it’s perfectly fine to use. For some reason, stores in my area are slowly getting rid of it…so this year I decided to make my own.

For the pineapple pie filling: In a pot, cook the crushed pineapple, cornstarch, sugar, and salt until thick. Add the butter and lemon juice. If using other fillings, cut recipe in half. And definitely do not double it. I don’t know what possessed me to do that, but I wound up with more pineapple pie filling than I could ever use.

Step 03: Once the dough has finished chilling, preheat your oven to 350°F. Flour your rolling pin (not too much, though, or it will make the dough difficult to work with) and roll out the dough on a prepared surface.

Cut the dough into 3-inch circles (a mason jar lid will work) and place the dough on a prepared baking sheet. Put a spoonful of pie filling on the circle. Roll the dough again, cut out more circles, and place those circles on top of the pie filling. Use a fork to press and seal the edges. Brush each cookie with milk and sprinkle with sugar.

 (Optional: use the large end of a turkey baster to cut little round holes into the top circle before placing it. That way, you can tell what each cookie is. Also, the filling won’t explode out of the sides when you seal them, because they’ll have some wiggle room in the center.)

Step 04: Bake for 12-15 minutes. Let cool on the cookie sheet for about 5 minutes and then move to a cooling rack.

Pie Filled Sugar Cookies was last modified: May 22nd, 2017 by Chelsey