Chocolate thumbprint shortbread cookies made with melt-in-your-mouth chocolate and a shortbread cookie crust.

A round brown plate of eight chocolate thumbprint shortbread cookies next to a wire rack of more of the same cookies. On the dark wood table there are several green, red, and silver wrapped Hershey kisses. One of the wrappers is open with a Hershey chocolate Kiss sitting in it.

These are not the popular peanut butter blossom cookies. I had to say that right off the bat. They look just like them, but there are no peanuts in this recipe.

I created this recipe because I wanted to recreate a chocolate thumbprint shortbread cookie my brother and I used to eat as kids after school.

Upon searching the internet I found they were called Keebler Sweet Spots. They came in packs of 4 on white, rectangle cardstock liner in a clear plastic package. This was in the mid 90’s, mind you, so it’s been easily 30 years since I last had them.

While these aren’t an exact copycat of those cookies, they are delicious little gems.

An overhead view of a round brown plate with six chocolate thumbprint shortbread cookies.

Picking a Chocolate Topping

I’ve made this recipe countless times with different chocolate toppings. I also used Ghirardelli’s Thumbprint Drops, not realizing they’re a flat version and more like a wafer.

I’ve used Hershey’s Kisses, which are my favorite.

Brach’s Chocolate Baking Stars were my least favorite because the flavor was too rich with a shortbread cookie that’s already pretty rich tasting.

I prefer the Hershey Kisses and their cool chocolate bite, but the choice is yours on which to use. I included them all on the recipe card.

A dark wood table with four chocolate thumbprint shortbread cookies and several Christmas Hershey Kisses.

Ingredients

Butter
Packed Light Brown Sugar
Egg Yolk
Pure Vanilla Extract
All-Purpose Flour
Salt
Hershey Kisses, Brach’s Chocolate Baking Stars, or Ghirardelli Baking Milk Chocolate Thumbprint Drops

How to make Chocolate Thumbprint Shortbread Cookies

Preheat oven to 375℉. Spray a cookie sheet with cooking spray or line it with parchment paper or a silicone mat.
Cream butter and brown sugar together in an electric mixer or with a hand mixer until it is light and fluffy. Add vanilla and egg yolk and mix on a low speed.
In a separate bowl, whisk together flour and salt. Slowly add the flour mixture to the mixing bowl and blend well on low.

A KitchenAid mixer with a silver mixing bowl and gray paddle attachment mixing shortbread cookie dough.

A large rectangle baking sheet with 12 cookie dough balls in 4 rows of 3.

Roll dough into 1″ balls and place them 1″ apart on a cookie sheet. I like using a small cookie scoop to get the right amount and then rolling it in my hands to get each one the same size.
Bake for 6 minutes. Remove the pan from the oven and press a chocolate Kiss or star on each cookie while it is still hot. Place it back in the oven for 2-3 additional minutes until the cookie is set.

A baking sheet with chocolate shortbread cookies being topped with Hershey kisses by a hand.

A metal wire cooling rack with eight chocolate thumbprint shortbread cookies.

Move cookies to a cooling rack until completely cooled. Store in an airtight container.

An overhead view of a round brown plate of eight chocolate thumbprint shortbread cookies next to a wire rack with more of the same cookies. Several Hershey Kisses sit next to it in red, green, and silver wrappers. An unwrapped Hershey Kiss sits next to the brown plate with a chocolate Kiss sitting on it.

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