Ingredients

For the Dulce de Leche
(this takes at least 6 hours to prepare for the cookies, so you better get it going!)
14 oz. Can of Sweetened Condensed Milk

For the Cookie
1 Cup Cold Butter (cut into cubes)
1 and ½ Cup Sugar
2 Eggs
1 Tsp Vanilla
2 and ¾ Cup Flour
1 Tsp Baking Soda
2 Tsp Cream of Tartar
¼ Tsp Salt

For the Cinnamon Sugar
2 Tbsp Sugar
1 tsp Cinnamon
(I usually just do however much I feel like and don’t measure, but this is what my recipe says, so it’s probably a fair guess at how much you’ll actually use)

Instructions

Make the Dulce: this preparation is pretty far ahead of the other things. You need to cover your can of sweetened condensed milk with water in a pot on the stove, and boil it at medium heat for 4 hours. You could also put the can in your crockpot on low for 10 hours, or high for 5 hours, just make sure it is always covered by the water. I personally like to do a couple cans while I’m going to such a long effort of making dulce. After it’s done cooking, put the can of dulce in the fridge to cool off.

Freeze the Dulce: once the dulce is cooled off in the fridge, open it and portion it out onto parchment paper in Tablespoon sized lumps. Put these in the freezer.

Cookie Dough: mix the butter, sugar, eggs, and vanilla together with your mixer until combined with butter chunks remaining. Add flour, baking soda, cream of tartar, and salt and mix until the dough comes together and no butter chunks seem to remain.

Assembly: Before you start assembling, preheat the oven to 375 degrees Fahrenheit. Start by getting two blobs of cookie dough that are about 2 TBS of dough each. Smoosh each one flat between your hands and lay softly on the table. Now get one of your dulce blobs and place in the middle of one of your smooshed doughs. Take the other smooshed dough and lay it on top with the filling in the center. Now press the two halfs of smooshed dough together around the filling, sealing off the filling center. Throw any bits of dough that aren’t needed back in the bowl with the dough. Try to compact your cookie into a nice ball, roll in your cinnamon sugar, and place on your cookie sheet. Repeat until all your dough is gone. Place the cookies a couple inches apart and bake for 9 minutes or until you feel a crust forming on top of the cookie. Let cool and enjoy!