Chocolate Fudge Cookies with Candy Cane Buttercream Filling

It seems I still have holiday baking on the mind. I wrote out a whole bunch of recipes I wanted to bake while I was home, many of which were holiday inspired. I even bought candy canes in order to make these peppermint buttercream filled fudge sandwich cookies and I’m only posting about them now (even though I did make them before the new year started). I also have a box of gingerbread pudding mix I intended to use somehow, but that didn’t really work out since I’m not sure you can still get the pudding mix now. Maybe I’ll wait ‘til next Christmas. Oh well.

So these here are fudge cookies with candy cane buttercream filling. Did I tell you I purposefully bought candy canes for this recipe? Well I did, and I’m not sorry either.

I don’t know why it’s taken me so long to make sandwich cookies. If you recall, these were my first sandwich cookies I ever made and they were freaking fantastic! I’m a little ashamed to admit that I stuffed my face with more than my fair share… but they were so good. I’m getting a little sidetracked. I want to talk about these fudgy cuties.

The dough was so dark and thick I just wanted to eat it by itself, but I held back, I wanted to make sure I got an even amount of cookies so I could sandwich them all together.

The frosting that goes between these cookies is pure peppermint perfection (some alliteration for you). It was kind of fun to mash the candy canes to make the dust, but it wasn’t fun to clean up. Note to self: make sure to double bag it with hitting things with a meat pounder.

These are definitely best when paired with a glass of milk because it softens the cookie a little bit and makes it kind of fudgier.

Chocolate Fudge Cookies with Candy Cane Buttercream Filling

Slightly adapted from Sally’s Baking Addiction

Makes 21 sandwich cookies

Ingredients

Fudge Cookies

1 cup + 1 tbsp. unbleached all-purpose flour

¼ cup unsweetened natural cocoa powder

1 tsp. baking powder

¼ tsp. salt

8 oz. semi sweet chocolate, chopped

2 eggs, room temperature

1 tsp. pure vanilla extract

5 tbsp. unsalted butter, room temperature

¾ cup dark brown sugar

¼ cup sugar

Candy Cane Buttercream Filling

(Please note I made half this batch and still had about 1/3 remaining, but I tend to be a little reserved when filling cookies)

12 tbsp. unsalted butter, room temperature

2 ½ - 3 cups powdered sugar

3 tsp. pure vanilla extract

1-2 tbsp. milk

½ cup candy cane dust*

*To make candy cane dust: place about 8-10 candy canes into a plastic bag and crush with a mallet or rolling pin—something hard and heavy. Place a sifter over a bowl and sift the candy cane bits through. Keep the larger bits for garnish if desired.

Directions

Preheat the oven to 350 F. Line a baking sheet with parchment paper. Set aside.

To make cookies: whisk together the flour, cocoa powder, baking powder, and salt into a medium bowl. Melt the 8 oz. of chocolate in a medium heat-proof bowl placed over simmering water. Stir occasionally until chocolate has completely melted. Take the bowl off the heat and set aside to cool. In a small bowl, whisk together the eggs and vanilla.

In the bowl of an electric mixer fitted with the paddle attachment, cream together the butter and sugars until light and fluffy. Beat in the egg mixture. In a steady stream, pour in the melted chocolate. Mix on medium speed until everything is completely blended together. You may need to scrape down the sides of the bowl a few times. Gradually add the flour mixture. Scrape down the sides of the bowl as necessary.

Take a medium-small cookie scoop and portion out the dough onto the prepared baking sheet. Space each dollop of cookie dough about two inches away from each other. Bake for about 8-10 minutes. The dough should still be a little soft when taken out of the oven. Allow cookies to cool on the pan for 5 minutes before removing to a cooling rack to cool completely. Repeat with remaining dough.

To make the filling: beat the butter on medium speed with the paddle attachment on a stand mixer. Gently add the powdered sugar. Beat in the vanilla. Pour in the candy cane dust and beat until completely incorporated. Scrape down the sides of the bowl and beat for another minute. Refrigerate the filling for about 5-10 minutes. Frost the bottoms of half the cookies with the filling. Place the remaining cookies, bottom side down, on top of the filling. Keep sandwich cookies refrigerated up to five days.