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Pumpkin Pie Surprise Cookies

by Jessie Daye

First published: November 10, 2017 | Updated: June 10, 2026

It just took me three hours to write this blog post and then I deleted it. I deleted it! deleted it! deleted it! Do I sound angry!? Ahhhhhhhhhhhhhhh. WHYYYYYYYY do we need this three finger swipe nonsense on the Macbook? I don’t want to push my homescreen to the right. I don’t like it. I don’t want to do it. I continue to swipe to the left by mistake and then it goes far, far away. It probably goes to that cloud. Whatttttt isssss the cloud? I don’t want to share with the cloud. I don’t like sharing. Please stop it. Stop it now. I want my text messages on my phone and my photos on my computer. I don’t want them in my car, on my ipod, on my TV, watch, clock, or remote control.

This is what I get for being a smart-ass in writing this post. The cookies were a huge pain in the ass. The frosting was a huge pain in the ass. The photography, editing, and blog post writing was a huge pain in the ass. Hell, these cookies are just pretty, OK? Beautiful, pain in the ass, delicious cookies. Thank you for stopping by and reading this post.

Have someone make these cookies for you. Seriously.

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Punch Me In The Face Pumpkin Pie Surprise Cookies

Butter Cookie Ingredients
1 cup butter
½ cup packed brown sugar
2 ¼ cups all purpose flour
Sprinkles

Royal Pain-In-The-Ass Frosting
3 tablespoons Meringue Powder
4 cups (about 1 lb.) confectioners’ sugar
4 + 1 tablespoons warm water

Directions
1. Line baking sheet with parchment paper and set aside.

2. Cream butter and sugar together in a stand mixer. Gradually add  2 cups flour. Mix well. Roll into a ball and wrap with plastic wrap and refrigerate for 1 hour until firm. Preheat oven to 325 degrees.

3. Sprinkle board with some of the remaining flour. Place dough on board and roll to 1/4 inch thickness. Press out cookies with triangle cookie cutter or cut by hand with a paring knife. You will need to full triangles and one triangle with a cut out center for each cookie. We cut our triangles by hand. Place cookies on the parchment lined pan. Re-roll dough scraps and press out additional cookies. If the dough gets too soft, place back into the refrigerator or place the entire cookie sheet into the refrigerator until the dough becomes chilled again. You don’t want the dough to become too soft or it will spread out as it bakes.

4. Bake at 325° for 10-12 minutes and let cool.

5. Prepare the Royal PIA frosting in a stand mixer. Beat all ingredients until icing forms peaks (7-10 minutes at low speed with a heavy-duty mixer, 10-12 minutes at high speed with a hand-held mixer). Remove 2/3 of the frosting and place into a separate bowl. This is going to be your orange filling color and we will need to add it back into the mixer later. 

6. Scoop out almost 1/2 of the white frosting in the stand mixer and place into a piping bag with a standard round tip. This will be your “whipped cream” frosting.

7. Add a tiny bit of brown food coloring gel to the remaining frosting in the stand mixer and mix until you have your desired shade for the “crust” frosting. Add this to a piping bag fitted with a petal tip and set aside.

8. Clean out your mixing bowl and add the remaining white frosting back into the bowl and now add your orange food color gel. Mix with one additional tablespoon of water until you get a more liquid orange frosting. This is going to be your “pie filling” frosting. Add this frosting to a piping bag fitted with a round tip and set aside.

9. Prepare your cookies by stacking them. One full triangle should be on the bottom. You can dab the top with a little frosting and add the second cookie, which is the triangle with a cut out. Fill with sprinkles and a little thankful to never make these cookies again note. (Kidding) Write something more appropriate. Now dab a little more frosting on this cookie and secure with the top full triangle cookie. 

10. You will now flood the top cookie so this means you have to make a border with the orange frosting then carefully flood the inside with more orange frosting. It should slowly flood the entire top if it is the right consistency. Allow to dry for at least one hour until it is hard to the touch. 

11. Once the orange pie frosting has hardened you will need to pipe the brown crust frosting at the base of the cookie so it looks like a pie crust. Finish each cookie with a dab of white frosting so it looks like whipped cream!

TIPS: Keep all utensils completely grease-free for proper icing consistency.

* For stiffer icing, use 1 tablespoon less water.

* When using large countertop mixer or for stiffer icing, use 1 tablespoon less water.

Pumpkin Pie Surprise Cookies

Author: Jessie Daye
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Prep 1 hour
Cook 11 minutes
Total 2 hours 11 minutes
Triangle-shaped butter cookies decorated to look like mini pumpkin pies with royal icing frosting and sprinkle filling.

Ingredients

  • 1 cup butter
  • ½ cup packed brown sugar
  • 2 ¼ cups all purpose flour
  • sprinkles
  • 3 tablespoons meringue powder
  • 4 cups confectioners' sugar about 1 lb.
  • 5 tablespoons warm water 4 + 1 tablespoons
  • brown food coloring gel a tiny bit
  • orange food coloring gel

Method

  1. Line baking sheet with parchment paper and set aside.
  2. Cream butter and sugar together in a stand mixer. Gradually add 2 cups flour. Mix well. Roll into a ball and wrap with plastic wrap and refrigerate for 1 hour until firm. Preheat oven to 325 degrees.
  3. Sprinkle board with some of the remaining flour. Place dough on board and roll to 1/4 inch thickness. Press out cookies with triangle cookie cutter or cut by hand with a paring knife. You will need two full triangles and one triangle with a cut out center for each cookie. Place cookies on the parchment lined pan. Re-roll dough scraps and press out additional cookies. If the dough gets too soft, place back into the refrigerator or place the entire cookie sheet into the refrigerator until the dough becomes chilled again.
  4. Bake at 325° for 10-12 minutes and let cool.
  5. Prepare the Royal frosting in a stand mixer. Beat all ingredients until icing forms peaks (7-10 minutes at low speed with a heavy-duty mixer, 10-12 minutes at high speed with a hand-held mixer). Remove 2/3 of the frosting and place into a separate bowl for orange filling.
  6. Scoop out almost 1/2 of the white frosting in the stand mixer and place into a piping bag with a standard round tip for the whipped cream frosting.
  7. Add a tiny bit of brown food coloring gel to the remaining frosting in the stand mixer and mix until you have your desired shade for the crust frosting. Add this to a piping bag fitted with a petal tip and set aside.
  8. Clean out your mixing bowl and add the remaining white frosting back into the bowl and add your orange food color gel. Mix with one additional tablespoon of water until you get a more liquid orange frosting. This is your pie filling frosting. Add this frosting to a piping bag fitted with a round tip and set aside.
  9. Prepare your cookies by stacking them. Place one full triangle on the bottom, dab the top with frosting and add the second cookie (triangle with cut out). Fill with sprinkles and a note. Dab more frosting on this cookie and secure with the top full triangle cookie.
  10. Flood the top cookie by making a border with the orange frosting then carefully flood the inside with more orange frosting. Allow to dry for at least one hour until it is hard to the touch.
  11. Once the orange pie frosting has hardened, pipe the brown crust frosting at the base of the cookie so it looks like a pie crust. Finish each cookie with a dab of white frosting so it looks like whipped cream.

Notes

Keep all utensils completely grease-free for proper icing consistency. For stiffer icing, use 1 tablespoon less water. Triangle cookie cutters or hand-cut shapes work for this recipe.

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Hi, I'm Jessie. 

I’m a Los Angeles mama, home renovator, and lifelong creative, sharing the things that make everyday life a little more beautiful. I believe food is one of the best ways to bring people together, which is why I love cooking: it turns an ordinary Tuesday into something worth remembering. From recipes I make on repeat to DIY projects, home design, and a little bit of real life in between — welcome to my corner of the internet. I’m so glad you’re here.

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