Oatmeal Sugar Cookie Cups w/Pumpkin Spice Kisses

The last couple of autumn seasons I started noticing mentions of a Pumpkin Spice Kiss. Pumpkin Spice? You have my full attention. However, these seasonal kisses are only available during Halloween and autumn holidays. This year I remembered to look for these little kisses and try them for myself.

The verdict?

SOLD!

I had October all planned out with pumpkin-themed posts, some children-friendly treats and other “things.” Where did the month go? I used to love October, November and December. The whirlwind of holidays and events. I think a lot of it had to do with that promise in the back of mind. That promise and looking forward to that one day I would be doing all these eventful and meaningful holidays with my own family. By family I mean that expectation that there would be children. Children, as it turns out, were not in the plans for me. And so the years have quickly flown by and my love for these types of holidays faded as did that vision of children.

Oatmeal Sugar Cookie Cups w/Pumpkin-Spice Kisses

I’ve only recently decided it was time for an attitude and outlook change. So, what does that have to do with Oatmeal Sugar Cookie Cups with Pumpkin Spice Kisses? Maybe nothing, and then, maybe something. It’s buying Halloween candy again and finding clever ways to use them besides just treats for trick-or-treaters.

I’ll admit it. I was skeptical about whether these Pumpkin Spice Kisses were worth their weight. I was pleasantly surprised and happy to find that they are not only worth their weight, but also worth the seasonal wait. The middle is cleverly filled with white chocolate. So, besides popping them in your mouth and letting them slowly melt on your tongue, what baking project can I do with Pumpkin Spice Kisses that will also let them maintain their kissable shape?

Oatmeal Sugar Cookie Cups w/Pumpkin-Spice Kisses

These little cookie cups held up well. I tested and toiled other forms and presentation, but none of them really held an alluring appeal. I tried it in mini whoopie pie pan, as drop cookies, and as cookies shaped into balls. All a big bust. However, using a mini-muffin pan like I did for pecan tassies or my favorite developed recipe for Mini Pumpkin Pie Cookies was promising. The shape held up with my recipe for Oatmeal Sugar cookies.

These cookies are bit off the path for what I usually like to make, baked good with nuts with the use of some fruit or vegetable(s). The oatmeal makes it feel wholesome. I reworked this recipe I’ve had since I was a girl in junior-high (they call it middle school now). Even though it’s been reworked, I will rework it again in the future to cut down on the fat. For now it’s good. It’s a sweet cookie and the pumpkin spice adds to that sweetness too.

What’s really notable about these cookie cups, besides the obvious Pumpkin Spice Kisses, is the overall texture. The outside has a crispy texture, biting on through the cookie it gently gives way into the candy middle and the rest of the chewy cookie underneath. Also, the generous use of cinnamon, both in the cookie dough batter and the crusted sugary coating lends a nice “bite.”

Some teenie notes:

• You need to freeze the kisses for a couple of hours to overnight. This helps so that the candy piece doesn’t fall apart into a puddle of goo in the middle of the warm cookie you’re going to press it into.
• Use two teaspoons of batter for each cup/well.
• To give the cookies an extra crispy (and sugary) texture on the outside, you’re going to dip the cookie dough ball in a sugar/cinnamon mixture.
• No need to grease or prep the mini-muffin pan. Let the cookies cool in the pan for about 2-3 minutes before gently nudging them to freedom by using a flat side spatula or butter knife to twist them ever so slightly so they release. THEN, lift the cookie cup out of the pan onto a flat surface where you will push a Pumpkin Spice Kiss into the middle. There, the Kiss will melt, become soft, and adhere to the cookie from the bottom of the Kiss.
• I found these Pumpkin Spice Kisses at Target.

Happy Halloween!

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Oatmeal Sugar Cookie Cups w/Pumpkin-Spice Kisses

Makes about 6 dozen

Ingredients

• ½ cup butter
• ½ cup shortening
• 1 cup sugar
• ½ cup brown sugar
• 1 teaspoon vanilla extract
•  
• 1 large egg
•  
• 1 cup all-purpose flour
• ½ cup whole wheat flour
• 1 teaspoon baking soda
• 1 teaspoon cinnamon
•  
• 1 ½ cups old-fashion oats
•  
• 2 tablespoons sugar, white or brown
• ¼ teaspoon cinnamon
•  
• About 72 Hershey’s Pumpkin Spice Kisses (1 ½ packages), in freezer for at least 2-3 hours or overnight

Method

1. You will need a mini-muffin pan, either 12 or 24 cup/well capacity.
2. Preheat oven to 350° In a bowl of an electric or stand mixer beat the butter, shortening and sugars until light and fluffy. Add vanilla extract and then the egg.
3. In another medium-sized bowl, combine the flours, baking soda, and cinnamon.
4. Add the dry ingredients to the butter/sugar ingredients in three batches, mixing only until combined.
5. Add the oats and finish mixing until incorporated.
6. Meanwhile, in a small bowl or saucer, combine the 2 tablespoons of sugar with the cinnamon.
7. Fill each mini-muffin cup with 2 teaspoons of cookie dough shaped into a ball. Dip one side of the dough ball into the sugar/cinnamon and place the ball into the mini-muffin cup with the sugar coating facing up.
8. Bake for 10-12 minutes (watch your baking time).
9. While the cookies are baking, unwrap the needed amount of Pumpkin Spice Kisses from their wrappers.
10. Remove freshly baked cookies from oven and allow to cool for 2-3 minutes in the pan.
11. Remove each cookie, placing on a flat surface and push a Pumpkin Spice Kiss into the middle of each cookie. Return finished cookie to a wire rack to cool completely.
12. Store cookies in an airtight container. © Images & content: Cristina A-Moore for TeenieCakes.com.

Teenie Notes

• Use slightly softened butter. You don’t want it too soft. If just removing from the refrigerator, place in microwave for 10 seconds.
• With a paper towel, wipe the insides of each mini-muffin well between sets.
• I used a mini-muffin pan that had 12 wells. Your total baking time for all the cookies will be greatly reduced if you have a pan that has 24 cups/wells. You will just need to work quicker when removing them from the pan and placing the kisses in each cookie.
• No need to grease or prep the mini-muffin pan. Let the cookies cool in the pan for about 2-3 minutes before gently nudging them to freedom by using a flat side spatula or butter knife to twist them ever so slightly so they release. THEN, lift the cookie cup out of the pan onto a flat surface where you will push a Pumpkin Spice kiss into the middle. There, the kiss will melt, become soft, and adhere to the cookie from the bottom of the kiss.
• Once the Pumpkin Spice Kiss has been set in the warm cookie cup middle, it becomes soft and easy to bite into.

Cristina A-Moore | Teenie Cakes

Oatmeal Sugar Cookie Cups w/Pumpkin-Spice Kisses