[VIDEO] Jack-O-Lantern Chocolate Coated Shortbread Cookie

You do not need any holiday or special occasion to treat yourself, so whether you are celebrating Halloween or not, there’s always a reason to make this cookie, and that is because you deserve it. So let’s make this adorable Jack-O-Lantern Chocolate Filled Shortbread Cookie

Halloween Cookie

Hi Guys! Are you celebrating Halloween this year? If so, how do you plan to celebrate it with all the social distancing measures that we all have to follow. I’m really interested to know, so leave a comment and let me know how you plan to celebrate Halloween this year.

I’ve mentioned before that I do not really celebrate Halloween, it’s not a thing when I was growing up in the Philippines, and although it is a thong here in Canada, I did not adapt it. I do not dress up for Halloween, although at some point I had been wanting to. I always wanted to dress up like a ballerina, I’m obsessed with those fluffy tutu dress. Anyways, I do not dress up but I celebrate Halloween with FOOD, just like how I celebrate any other occasion. So it almost feels like a holiday in my house everyday with the different food I cook and bake for my blog. But this Jack-O-Lantern Shortbread Cookie, I make them during Halloween. It’s such a nice and fun cookie to share with friends. However, I use this same shortbread cookie recipe for other occasion, like my favorite Christmas, the time when cookies shows up on my desk like there’s no tomorrow.

Halloween Shortbread Cookie

I love this Pumpkin cookie cutter that I bought last year, and so I just kept on using it. I made a Pumpkin shaped Hand Pie last year which was well received and loved by my friends. They had fun choosing the character of the pumpkin that fits their personality. I got to chose mine too, I was the naughty Pumpkin.

I used the same technique in making this Pumpkin shaped Shortbread Cookie, it is a bit more work than the Pumpkin Hand Pie but I had fun making it. After all, with the travels and outings cut down, I have more time to work on my cooking and baking. So this Pumpkin shaped shortbread cookie kept me company and busy.

There is no Pumpkin on this cooked, just so you know. It’s just the shape. This is a shortbread cookie dipped in melted chocolate and filled with white chocolate. How does that sound to you? Chocolate in every bite, you are going to love having this for Halloween or anyday of the year. Your friends will also have fun with this cookie. 

So, how about I take you through the process now and let’s make this Jack-O-Lantern Shortbread Cookie? Let’s get started! 

My Other Cookie Videos

Not feeling like having a Shortbread Cookie, check out my other cookie videos for inspiration.

Use the Best Quality Ingredients

The steps are very simple, the ingredients are very basic, you only have few key things to remember if you want to have a nice buttery crisp smooth shortbread cookie. Since this cookie does not have a lot of ingredients, a lot of the taste will be coming from the butter and vanilla extract for flavoring. So, use a good quality butter and only pure Vanilla Extract (if using). Last but not the least, a good quality chocolate please, this is a MUST. Spending few more money for a good quality ingredients can go along way.  Let’s get started!

Jack O Lantern Shortbread Cookie

3 Ways to Make this Cookie Dough

This dough can be made using a stand mixer, hand mixer or food processor. The instructions below uses a stand mixer, while the video uses food processor. As you can see, using food processor is the easiest way to make this cookie dough. But you do not have to have one, a stand mixer or hand mixer is the common way most people do it. The only difference is the state of the butter. When using stand or hand mixer, use softened butter. This will allow the mixture to combine easily. While when using food processor, since it can easily handle hard butter, cold butter is the best one to use. Food processor method is simply putting all ingredients in the processor. Here is how you do it.

Make Shortbread Cookie With or Without Food Processor, It’s Possible

Using Food Processor – Recommended

There are two ways in which I normally make my shortbread cookie, but often times I used my food processor to make the dough. Using a food processor allow me to use a really cold butter that’s straight out of the fridge. Using cold butter makes the dough firmer and more manageable, it lessen the spreading of the cookie and early browning of the cookie during baking. Oftentimes, I don’t even have to chill the dough as it is good enough to to immediately roll and cut. But there’s exception, Summer time! Yes, I find that making a mostly butter based cookie is tricky when the weather it hot. The heat in the kitchen soften the dough quite easily, which means more chilling is required before rolling and cutting it. But that’s me really an issue here, we only have 4 months of warm weather, and there’s always my fridge to help me chill the dough. So, if you have a food processor, take it out and make use of it to make Shortbread Cookie. It will be such an easy breezy process.

Hand Mixer

Don’t worry if you don’t have a food processor, you can still make this Shortbread Cookie. Use a room temperature butter and use a hand mixer instead. Hand mixer should be able handle soften butter without any problem. The downside of this method is that the dough will require chilling to make it easier to handle. The cookie dough will be soft and it will be sticky to roll and cut, and so chilling is mandatory. Simply chill the dough in the refrigerator until it is manageable for rolling and cutting. You will know if it was chilled properly when it doesn’t stick to the rolling pin or on the surface when you start rolling it, or when it doesn’t break or tear easily. You can also use a soften butter in food processor, just remember when a butter is soften you will need to chill the dough, ALWAYS!

Shortbread Cookie

Tips in Making Shortbread Cookie

  1. Sift the Confectioner’s Sugar: Icing Sugar or confectioners sugar tends to have lumps, so sifting is recommended for a smoother cookie texture. Sift the sugar first using a flour sifter of a regular sieve then measure the required amount.
  2. Chill the Dough After Cutting: Regardless if you use soften butter or cold butter, it is still suggested that you chill the cut cookie in the freezer at least 15 – 30 minutes. This is VERY important to help retain the shape when you bake the cookie. A soft cookie when baked will spread a lot, resulting to a thin cookie, and worst a deformed cookie.
  3. Same Size, Same Thickness: It is very important to have the same size and thickness for the cookies so that they all bake at the same time. If you have some thicker and bigger than the other, it will not be bake the same time as the other pieces.  1/4-inch thickness is the ideal thickness for this cookies. Make it too thin and it will get burnt or crunchy too soon. You can use a ruler to measure the thickness. Sometimes it is quite easy to spot a thin cookie once you get the hang of making it. I would say thicker is better than thinner. Thicker will require more baking time, but at least it will not burn as easily when you have it thin.
  4. Do NOT Over Bake: You’ve probably heard this countless times when making a cookie, Do NOT over bake. Bake at 18 – 20 minutes only, check at 15 minutes mark. If the side starts to brown already while the center is still white and soft, that is ok. Shortbread cookie are very fragile cookie, plus it is a butter based cookie which makes it susceptible over baking if not monitored. Take the cookie out when you notice the side starts browning while the top is still pale. The cookie will continue to cook as it cools. Baking time should be adjusted if baking a frozen shortbread cookie straight from the freezer. Add 1-2 minutes (more or less).

Can I Use Granulated Sugar Instead of Icing Sugar

Technically, you can but the texture will NOT be the same. Icing sugar have a fine powdered texture that makes the cookie smooth and creamy. It also blends well, and dissolve easily thus producing a better cookie texture.

Pumpkin Shaped Shortbread Cookie


  • 1/2 cup (1 stick) unsalted Butter – softened at room temperature (If using a food processor, use COLD butter)
  • 1/4 cup Confectioner’s /Icing sugar (Sifted – Sift first before measuring)
  • 1 cup All-Purpose Flour
  • 1/8 teaspoon Salt
  • 1/2 teaspoon Vanilla Extract (optional)
  • 1/3 cup Dark Chocolate – melted
  • 1/4 cup White Chocolate – melted


  1. Preheat oven to 350F. Prepare a silicone mat or baking sheet lined with parchment paper.
  2. Food Processor Method: Add all ingredients in the food processor and process until dough start to clump together, about 2 minutes.
    • Stand Mixer or Hand Mixer Method: Alternatively, you can do this using a hand mixer or stand mixer but you have to use a softer butter so it mix easily. Chilling time will be longer (about 30 minutes) as the cookie will be softer.
  3. Chill the Dough  Take the dough out and form into a cohesive ball. Wrap with plastic wrap and refrigerate for 15 minutes.
  4. Shape and Cut: Take the dough out of the refrigerator. Unwrap, and place the plastic wrap on top as you roll the dough, this will prevent sticking to the rolling pin. Roll the dough to about 1/4-inch thick. Using a pumpkin shaped cookie cutter, cut 12 pieces. Gather excess dough and use to cut remaining pieces. If the dough feels soft, pop in the refrigerator to chill and harden a bit.
  5. Chill: Transfer in a baking try and chill in the freezer at least 15 minutes. This will make it easier to carve and will also help the cookie to hold its shape while it bakes. Do not skip this step as it is crucial to retaining the cookie shape as it bakes.
    • Alternatively, You can also freeze the cookie dough up to 3 months. Shape before freezing. No need to thaw when ready to bake.
  6. Carve: Remove from the freezer and carve one piece at a time. Leave in the freezer the pieces that you will not be working on yet. Transfer the piece on top of a chopping board lines with parchment paper. Using a toothpick or a BBQ stick, draw on the cookie, this will be your guide when you carve it. Once done, use a sharp knife to carve the cookie. return the carved piece in the freezer and continue with the rest of the 5 pieces. You only need to carve 6, the other 6 pieces will be the base so leave it as is.
  7. Bake: Bake for 15 minutes, or until the edge of the cookies starts to turn slightly brown. Keep an eye on the cookie as it could get burn easily. Some spots could end up browner especially the thin portion of the cookie because that will tend to cook faster. But do not worry, the cookie will be dipped in chocolate later. Rotate the pan half way the baking time. Let cool on baking sheet for 5 minutes then transfer in a cooking rack. Be careful in lifting it as the cookie is fragile.
  8. Dip in Dark Chocolate: Microwave the chocolate in 30 seconds interval and stir after each interval. The chocolate should be smooth and fully melted. Dip the front side of the carved cookie in melted chocolate, then arrange in a parchment lined pan. Dip the back side of the base cookie and arrange as well in a parchment line baking sheet. When doing this, make sure to gave the front and back paired together so you can identify which side to dip in chocolate.
  9. Fill Center with White Chocolate: Microwave the chocolate in 30 seconds interval and stir after each interval. The chocolate should be smooth and fully melted. Once the dark coating is solid, arrange the cookies in pairs, then spread white chocolate in he middle of the base cookie. Cover with the carved cookie on top. This is like a sandwich shortbread cookie.
  10. Refrigerate: Keep the cookies refrigerated until ready to serve.

Makes 6 cookies

How to Freeze Shortbread Cookies

One of the thing I like about shortbread cookie is it freezes well. To freeze the shortbread cookie, you have two options to do this.

  • Shape & Freeze: Cut the cookie into desired shape (pumpkin shape in this case). Arrange in a parchment lined bakig sheet and freeze for at least 30 minutes. Transfer in a container or ziplock bag with parchment paper in between stacks. Freeze up to 3 months. No need to thaw when ready to bake.

Nutrition Information

Nutritional Information was calculated using Veryfitwell Recipe Calorie and Nutrition Calculator. For details about Nutrition Information in this website, please read the Nutrition Disclaimer page.

Recipe Notes:

  • Remember, size and thickness matters. The bigger and thicker your cookie, the more baking time you  need. So, adjust your baking time accordingly.
Shortbread Cookie

Shortbread Cookie Variation

Basic Shortbread Cookie

This is where it all begun. Simple, classic shortbread cookie. Creamy, butter and simply addictive.

Chocolate Dipped Shortbread Cookie

Smooth and creamy Shortbread Cookie dipped in a decadent melted dark chocolate, a treat in ever bite.

Strawberry & White Chocolate Shortbread Cookie

Strawberry & White Chocolate Shortbread Cookie is a lovely delicious twist to my classic Shortbread Cookie recipe. The base is a creamy, buttery shortbread cookie with a layer of white chocolate and Strawberry paste and finish off with slice of fresh Strawberry coated with white chocolate. Every layer of this shortbread is perfection, they just seem to work well together.

Matcha Glazed Shortbread Cookie

This Match Glazed Shortbread Cookie has a smooth, creamy and buttery texture plus a heavenly white chocolate matcha glazed on top. Yes, it is over the top sinfully delicious just like my other Shortbread cookie recipes. Shortbread cookie is one of my favorite cookie of all time. For me, nothing beats a simple satisfying cookie that always comes out perfect. There’s no hit and miss here, what you see is what you get.

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