Preheat your oven to 350°F (175°C) and line two 8x4” loaf pans with parchment paper.

In a mixing bowl, cream softened butter, white sugar, and brown sugar together on medium speed for 3–5 minutes until light and fluffy.

Add eggs one at a time, beating well after each addition along with the peppermint extract for about 2 minutes.

Whisk together flour, cocoa powder, baking powder, baking soda, espresso powder, and salt in a separate bowl.

Gradually mix half of the dry mixture into the wet ingredients, then add the milk and mix until just combined.

Alternate with the remaining dry ingredients and fold in dark chocolate chips.

Divide the batter between the prepared loaf pans, filling them about two-thirds full.

Bake in the preheated oven for 45–55 minutes, checking for doneness with a toothpick.

Let the loaves cool in the pans for about 10 minutes, then transfer to a wire rack to cool completely.

Whisk together powdered sugar, milk, peppermint extract, and Greek yogurt until smooth for the glaze.

Spread the glaze over the cooled loaves and sprinkle with crushed candy canes.