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Caramel stuffed, chocolate topped, butter thumbprint cookies are rich, delicious, and perfect for the holidays!
Food and holidays go hand in hand. The baking, cookie making, and desserts are a huge part of my holiday memories.
When I was younger my family always made candies during the holidays, toffee, brittles, and other more technical treats. I loved the end results, but as a kid I remember feeling a little left out of the fun. I understood that you had to cook to a specific temperature, and measurements had to be exact for the candies to come out the way they were intended, but I wanted to be included.
Now, as a mom I know that my kids are not going to be as exact, or pay close enough attention to cook my caramel to soft ball stage. So instead of making candies, my kids and I spend our holidays baking cookies, like these super easy and so insanely good thumbprint cookies, as well as making really easy, no bake treats like chocolate covered bananas, and we use Smucker’s Toppings to make things really easy.
So to get started, I just ran to Target, and while I was eyeing all the holiday décor and super cute clothes (yeah, I pretty much exclusively wear Target these days, it is just so convenient to shop for groceries and clothes and diapers in the same place), I headed to the grocery section to grab baking supplies, and Smucker’s toppings.
And, another perk! There is a Cartwheel Deal for the Smucker’s Toppings!: Smucker’s Toppings are 20% off, Running 11/29 – 12/12:
Then we headed home to bake! Trust me, whether it is for a cookie exchange, a family party, or a little personal indulgence, making these cookies is going to make your year! They are super yummy, and way easier to make than you would think.
You start with a basic butter thumbprint cookie recipe.
Roll it into balls, and push down the center to form a thumbprint.
Then you bake the cookies, and fill the thumbprint with Smucker’s Sugar Free Sundae Syrup Caramel.
Then pour Magic Shell over the top, and a sprinkle of large crystal salt.
You get the soft, rich, buttery, cookie, the delicious caramel, and a bit of crunch with the magic shell chocolate! Delish.
My kids loved being able to be part of the process, pressing down the center indentation, and filling the baked cookies with caramel, or shaking the Magic Shell until it was ready to pour. So we were making memories!
While I loved making these, another one of my favorite ways to use Magic Shell is chocolate covered bananas! I can’t eat the frozen ones, they hurt my teeth, so instead, I use Magic Shell to cover the bananas, and top with crushed peppermints, sprinkles, and other fun holiday themed goodies!

Chocolate Covered Caramel Thumbprint Cookies
Ingredients
- 1 cup salted butter softened
- 1/2 cup confectioner's sugar
- 11/2 tsp vanilla extract
- 1/2 tsp butter flavoring optional
- 1/4 tsp kosher salt
- 2 cups all purpose flour
- 1/2 cup Smucker's Sundae Syrup Caramel
- Magic Shell
- Large Crystal Salt
Instructions
- Preheat oven to 325 degrees F.
- Cover a cookie sheet with parchment paper
- Using a stand mixer with a paddle attachment, cream butter and sugar together. Mix for 2 minutes.
- Add in vanilla and salt, and butter flavoring (if using) scrape down sides of bowl.
- Add in flour, mix until just combined.
- Use a tablespoon measurer to scoop out a heaping TBS ball of dough, and place it on the parchment sheet. Then depress the center either with a smaller measuring spoon or your thumb.
- Bake 12-15 minutes until golden brown and puffy.
- Remove from pan and let cool on wire rack.
- Fill center with Smucker's Sundae Syrup Caramel
- Place on a cooling rack over the top of a piece of parchment, and coat in Magic Shell. Shake the Magic Shell well, and squeeze over the top. The excess will run down the sides and pool on the parchment. That is okay. You just want to cover the outside
- Before Magic Shell hardens, sprinkle a little large crystal salt on
- Keep in airtight container until ready to eat. Good for 3 days.
Nutrition
Our recipe card software calculates these nutrition facts based on averages for the above ingredients, different brands, and quality of produce/meats may have different nutritional information, always calculate your own based on the specific products you use in order to achieve accurate macros for this recipe.

Be sure to check out more delicious Holiday recipes at Smucker’s. I’d love to hear about your favorite Holiday recipe!
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