Preheat oven to 350° F. Grease a mini muffin pan with cookie spray or Crisco.
Allow butter to come to room temperature for about 30 minutes. Combine butter and sugars in your stand mixer and beat on medium speed until light and fluffy.
Add eggs and vanilla extract. Beat into butter and sugar until thoroughly mixed.
In a medium sized bowl, combine flour, cocoa powder, dry pudding mix, baking soda and salt. Stir to combine. Set aside.
Slowly add dry ingredients into batter and beat on a low speed until dough starts to form. If dough is a little dry, add 1 tablespoon of milk. Set dough aside.
Use a food processor to grind graham crackers into a fine crumb.
Melt butter in a microwave-safe bowl until melted. Combine melted butter with graham cracker crumbs and stir until there are no dry crumbs lefts.
Spoon 1 tablespoon of graham crackers into the bottom of the mini muffin pan. Press down with a spoon or tart shaper.
Drop 1-1.5 tablespoons of dough into the greased mini muffin pan on top of the graham crackers. Bake at 350°F for 12-15 minutes.
Remove cookies from oven and allow to cool for at least 5 minutes. Use a tart shaper or the back of a spoon to gently push down the middle of the cookies. Allow to cool for another 30 minutes in the pan. You may need to run a knife around the edge of the cookies to help release them from the pan. Cool completely.
There are two options for the marshmallows. You can melt them on parchment paper in the microwave, or you can toast them in the oven. If using the microwave, use a piece of parchment paper or silicone mat, and melt for 10-15 seconds until the marshmallow puff up. Remove from microwave and transfer onto the top of the cookies with a knife. If you have a kitchen torch, lightly torch the marshmallows.
If using the oven, increase heat to 425° F toast on the top shelf until golden brown. Transfer to cookies with a knife.
Notes
Cookie recipe adapted from somethingswanky.com. I have a large mini muffin pan, but if you are using a regular sized mini muffin pan, I suggest to reduce the graham cracker crust and dough slightly.
Recipe by Chef in Training at https://www.chef-in-training.com/smores-cookie-cups/