For the Streusel:
Preheat oven to 325Β°F (165Β°C).
In a small bowl, whisk flour, granulated sugar, cocoa powder, and salt.
Pour butter over flour mixture and mix with a fork or your fingers to make crumbles.
Spread mixture on a parchment-lined baking sheet.
Bake streusel, stirring every 5 minutes to prevent burning, until firm and a milk chocolate shade of brown, about 15 minutes.
Let cool.
For the Ganache:
Place chocolate in a medium heatproof bowl.
In a small saucepan over medium heat, heat cream just until it starts steamingβdo not let it boil.
Pour hot cream over chocolate and let sit 10 minutes.
Stir until melted, smooth, and a creamy consistency is reached.
Let cool.
For the Cookie Dough:
In a medium bowl, whisk flour, cocoa powder, cream of tartar, baking soda, baking powder, and salt.
In a large bowl, using a handheld mixer on medium-high speed, beat butter and granulated sugar until light and fluffy.
Add egg, egg yolk, and vanilla and mix until incorporated.
Add dry ingredients and beat on medium-low speed until no flour remains.
For the Cinnamon Swirl:
In a small bowl, mix brown sugar, butter, cinnamon, and salt to form a paste.
Dollop over dough and stir in with a rubber spatula to create streaks.
Be sure not to overmix so the streaks remain while baking.
Portion dough into 10 pieces (about 3.5 oz each).
Roll into balls with your hands.
Arrange between 2 parchment-lined baking sheets.
Refrigerate until cold, about 1 hour.
Preheat oven to 350Β°F (175Β°C).
Bake cookies until edges are set, about 15 minutes.
Let cool 20 to 30 minutes.
Spread ganache over cookies.
Sprinkle with streusel.
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