Before shaping, I chill the dough for about 15 minutes. It makes it easier to roll into smooth balls without sticking to my hands. When I place them on the baking sheet, I gently press my thumb—or the back of a measuring spoon—into the center of each ball to create a perfect well. You want to press firmly enough to hold the filling later, but not so deep that you break the base of the cookie.
While the cookies bake, I prepare the chocolate fudge filling. This part always makes the kitchen smell like a cozy chocolate shop. I warm the cream until it’s barely simmering, then pour it over the chocolate chips and butter. After a minute, the mixture melts into a glossy, decadent filling. Once the cookies come out of the oven, I let them cool for just a few minutes before spooning the warm chocolate into their centers. As it sets, it develops a soft fudge-like texture that pairs beautifully with the crisp peppermint topping.
Pro Tips for Best Results
I tested this recipe three different ways before settling on what I now consider the perfect method. One thing I learned quickly is that peppermint extract is strong—very strong. A little more than half a teaspoon can push the flavor into toothpaste territory. So I always measure it carefully and never eyeball it.
Another thing I learned the hard way is that crushed candy canes vary wildly in size depending on the brand and how you crush them. Larger chunks tend to melt too quickly, creating sticky patches around the edges. For the best result, I crush them finely with a rolling pin, aiming for pieces no larger than sesame seeds. It distributes the flavor better, too.
I also discovered that letting the cookies cool slightly before adding the chocolate filling helps prevent it from melting into the cookie well too quickly. You want the chocolate to sit neatly without turning into a puddle. Waiting just two or three minutes makes a difference.
Finally, don’t skip the chilling step. I tried skipping it once when I was in a hurry, and the cookies spread so much they looked more like peppermint pancakes. Chilling keeps them shaped, structured, and picture-perfect.
Common Mistakes to Avoid
The first mistake I made was overbaking these cookies. Thumbprints don’t brown much, so it’s easy to think they’re underdone. But if you wait for golden edges, the cookies will turn dry and crumbly. Instead, pull them out when the bottoms are just set and the tops still look pale.
Another mistake is filling the thumbprints while the cookies are still scorching hot. The chocolate filling becomes too thin and runs right over the edges. Let the cookies cool for a few minutes so the chocolate stays where you want it.(See the next page below to continue…)