1 cup flour
1/3 cup cocoa powder
1 cup icing sugar
3/4 cups unsalted butter
4 Tbsp orange juice
1 can sweetened condensed milk
4 squares semi-sweet chocolate
4 Tbsp butter
A night or two before you plan on making the cookies, you are going to make the easiest,most flavorful caramel in the universe that you'll eventually spread on the cookies. Take a can of sweetened condensed milk (I used two incase I messed up the recipe royally and had to make them again.
Note: Picture shows 2 cans of sweetened condensed milk but this recipe only requires 1. I used an extra can just for backup.
Take the paper off of the can. Add to a large pot of boiling water (Do Not Open The Can), making sure they are submerged the entire time. Let the water come down to a simmer and leave for 2.5 hours. After 2.5 hours put in the fridge (after they’ve cooled down a bit) for at least over night and no longer than a week.
Preheat the oven to 350F and lightly grease cookie sheets.
Take the can of caramel out of the fridge to bring it up to room temperature.
Sift flour and cocoa powder.
Cream butter and sugar until fluffy.
Add orange juice and eggs and combine.
Add dry ingredients slowly and combine until smooth (it kind of looks like frosting).
Put mixture into a pastry bag with a large flat tip. Pipe into overlapping ribbons, about 4-5 per cookie. I'm bad at piping, hence the ugly little mishapen cookies.
Also remember to space them out or you will have to cut them apart as I did.
Put into oven for about 5 minutes. Check to see that they are not burning. When the liquid middle begins to harden, take cookies out (it happened in 2 more minutes for one batch, another five for the other batch).
Remove from cookie sheet carefully and put on cooling racks to cool completely (the cookies are a little flimsy at this stage and you will melt the caramel too much if you spread it on now).
Now open the cooled milk cans. Behold the sweet sweet caramel.
When completely cool, spread the caramel over one cookie and make a sandwich with another cookie. How much caramel you use depends on how much you like. I like adding an amount somewhere between a hearty slop and a thunderchunk.
What a cookie should look like:
Now for the glaze:
To make the glaze, chop the four blocks of chocolate with a serrated knife or a chocolate fork if you have one.
Add to a glass or metal bowl over a pot of simmering water and put in the 4 tbsp pf butter.
Once melted completely and smooth, spoon over one side of the cookies.
You can do both if you want, but I find it too messy and it tastes pretty good with just one side done. Put cookies in the fridge for the glaze to harden, then enjoy.