Make your dolce de leche first – this could even be made the day before.
Remove the label from a can of sweetened condensed milk. Fill a large pot with water (one large enough to fully submerge the can of condensed milk) Place the can into the water on its side, making sure it is covered by at least 2-3 inches of water. Bring the pot to a boil over medium-high heat.
Once boiling you are going to cook the can of condensed milk for 2-3 hours (depending on how caramelized you want your dulce de leche. For this cookie cake I let mine cook for 2 hours. Be sure to check your pot of boiling water every 20-30 minutes to make sure the water is still above the can. You will most likely need to top it off every so often. Try not to let the water level go below the can as this might cause it to cook unevenly.
Once the 2-3 hours is up, remove the can from the water and place on a wire rack to cool completely to room temperature. Do not try to open it while it is still hot / warm, as the pressure inside will just result in the dulce de leche oozing out all over the place. Be patient – it’s worth the wait.
Chocolate Mocha Cookies
While your dulce de leche cools; make your cookies.
Preheat your oven to 350 degrees regular or 325 convection if possible. (Convection is my
favourite way to bake cookies) Line two large baking sheets with parchment paper.
In a large mixing bowl, cream together butter and sugars until pale and creamy. Add in your egg and beat on high until fluffy. Add in your vanilla, milk and espresso powder; mix on high until combined.
In a small bowl, whisk together flour, baking soda, salt and cinnamon. Add dry ingredients to the wet ingredients and beat on low until it starts to come together; increase the speed and beat until completely combined. Beat in your chopped dark chocolate and mix to combine.
Use a large cookie scoop to portion the dough into 10 large balls – and I mean large, they should be about 100g each in size. Distribute them onto two prepared baking sheets; place them in the freezer for a quick 10 minutes each before baking.
Bake the cookies 1 pan at a time. Bake them for 10 minutes, and spin the rack around in your oven.
Let them cook another 4 minutes or so or until the edges are a light golden brown. In total your cookies will bake for about 14-15 minutes. For the purposes of this cookie cake recipe, it’s best if your cookies are a little underbaked, so don’t worry if the centers don’t look quite set, they will continue to cook once you remove them from the oven.
** Tip: If you want to create a crackly top on your cookies, at the 10 minute mark, lift one side of the pan a few inches off the rack and let it fall; repeat this process a couple of times before shutting the oven door and allowing your cookies to continue to cook. You will notice that your puffy cookies will have sunken a little bit – this is what you want. Repeat this process every 2 minutes until your cookies are baked. This is what will create those tasty looking crackles.
Remove your cookies from the oven and allow them to cool completely before assembling your cookie cake.
Assembly
Once your cookies and your dulce de leche are completely cooled, you are ready to assemble.
This recipe makes 10 cookies, but I usually just use 8 fore my cookie cakes.
Place your first cookie onto the plate that you would like to serve it on. Spoon about 1 tbsp of the dulce de leche on top and use the back of a spoon or an offset spatula to spread it to the edges, leaving a little bit of a border, as the dulce de leche will spread more on its own as you continue layering.
Repeat this process with the following 6 cookies, being gentle as you add each layer and spread on your dulce de leche. Place the final cookie on top; allow the cookie cake to sit for at least 15 minutes just to let the dulce set up so that it is easier to cut into. Use a sharp knife to dig in!