Chocolate Chip Cookie Cannoli

So... I'll leave that right there for you to look at...

To say that this is a simple recipe would be a lie. Well, sort of a lie, the recipe is easy but the execution takes patience and probably a full afternoon but these are so incredibly worth the time and energy you put into them. These are so good, the dough makes an amazing crunchy on the outside while chewy on the inside cookie and the whipped cream filling perfectly offsets the sweetness of the cookie in a "cookies and milk" sort of partnership!

I'd love to say I was researching Italian desserts and came up with this fully thought out and amazing creation but in all reality I just thought this would be cool and then it happened to work out after some trial and error (mostly error).

Here are some step-by-step pictures to help with the confusing instructions:

I started with a roll-out chocolate chip cookie dough which is different from a regular chocolate chip cookie dough because, like sugar cookie dough, it will stay put if you want to use cookie cutters on it. Here is a photo of the dough:

Then I rolled out the dough to about a quarter inch thickness by placing it between 2 pieces of parchment paper. If I was to make this again I would probably use mini chocolate chips to get a better distribution of chips throughout the dough.

Then, since I don't own any cannoli forms, I took a piece of aluminum foil and folded it over about 3 times until it was around 5 inches wide and 12 inches long and used my two index finders to roll up the foil (kind of like a Chinese finger trap). Then I cut a 3 inch by 5 inch rectangle of dough to roll up around the foil tube, which I sprayed with cooking spray.

After that I took another rectangle of aluminum foil, sprayed it with cooking spray and rolled it around the dough roll... here is a photo of that step and I apologize for the quality.

Next, I baked the cookie rolls/tubes/cannoli at 375 degrees for about 20 minutes, turning them a quarter turn every 5 minutes making sure each side got even cooking. After they were done cooking I unrolled the outer foil to check that there was no raw dough, if there was I re-rolled the foil around the dough and placed the raw portion of the dough facing down on the cookie sheet for another 5 minutes. I allowed the cookies to cool completely before unwrapping and filling them. 

While the cookies were baking I whipped up some heavy whipping cream that was light on sugar since the cookies are so sweet and put it in the fridge until the cookies were cool. When the cookies were completely cooled I put the whipped cream into a freezer size ziplock bag, cut the corner off, and filled the cannoli. To fill the cannoli fill one half of the cannoli from one end and then fill the other half from the other end to make sure the filling is evenly distributed. 

You can leave the cannoli just like that and they are fabulous:

Or you can drizzle melted chocolate and sprinkle powdered sugar on top to really take these over the edge:

Here is how to make these beauties-

Ingredients for Dough:

• 1 Cup- Unsalted Butter at room temperature
• 1/3 Cup- Granulated Sugar
• 1/2 Cup- Packed Brown Sugar
• 1 large egg yolk
• 2 tsp Vanilla Extract
• 2 Cups- All Purpose Flour
• 1/2 tsp- Salt
• 1 Cup- Semi-Sweet Chocolate Chips

Ingredients for Whipped Cream Filling:

• 1 Cup- Heavy Whipping Cream
• 1 Tablespoon- Granulated Sugar

Instructions:

1. Preheat oven to 375 degree Fahrenheit
2. Cream together butter and sugars until creamy then add egg yolk and vanilla until everything is combined
3. Sift salt and flour together and add to wet ingredients one cup at a time until just combined
4. Mix in chocolate chips
5. Roll out dough between 2 pieces of parchment paper to 1/4 inch thickness
6. Cut out 3 inch by 9 inch rectangle and roll around a 1/2 diameter 5 inch with tube made out of aluminum foil or use cannoli forms
7. Roll large rectangle of aluminum foil around outside of rolled up dough
8. Bake for 20 minutes, turning a quarter turn every 5 minutes
9. Remove from oven and place on cooling rack until completely cooled.
10. While cookies are cooling whip cream and sugar together for about 5 minutes until firm and put in refrigerator until ready to fill (I over-whipped my cream slightly so that it would be a sturdier filling)

Filling:

1. Put whipped cream into larger ziplock bag and cut off the tip to fill (you could also use a pastry bag)
2. Fill one half of the cannoli from one end and then fill the other half from the other end

Optional:

Top with melted chocolate chips and/or powdered sugar

Hopefully, after all of that you have a perfect dessert to indulge in. If it didn't work out at least you can eat some cookie dough, right?!