Dessert · sugar 2.0

Rookie Error – Chocolate Pudding Pockets

Rookie Error…..

Today’s recipe is reworked from one of the recipes that I created about two years ago. I made it, posted it, and just over the last month I noticed that I have suddenly had a lot of people looking at it. I looked at it again, and knew that I need to take better pictures, but then I looked at the recipe itself. I don’t even know how that disaster happened, but my apologies to anyone who looked at it and possibly tried to make it. I can’t even count the number of mistakes that were in it. From terrible pictures to mismatched ingredients this poor recipe was an absolute disaster. So, for those who may have looked at it before and cringed I hope you will come back and peek at the new and IMPROVED version.

pudding pockets3The reason I created this recipe is because when I was a kid these were one of my all-time favorite treats. My mom was always making sweet treats of some kind, but she surprisingly never made these. My memories come from a company we all know, Hostess. Hostess has been producing pudding and fruit pies since the 1980’s. (One more memory the 80’s will leave with us.) I will admit that they are far from a healthy treat, and I heard rumors that they’ve changed their recipe so they don’t even taste that good any more. I can assure you that these taste exactly like the pies we grew up with and even though I used butter in the crust, over all, they are much healthier then the store bought version.

pudding pockets7I’m going to give you a few tips that should make these super easy hand pies, or pudding pockets, a breeze to make. I’ve made them dozens of times, and I can assure I have had just about every fail possible.

  1. Make the pudding filling and allow it to cool. If you try to put hot filling inside the crusts it spreads and seeps out the edges and it just looks yucky. And while they are still edible, when you go to eat them the insides are empty and most of the pudding is left on the pan.
  2. Chill your dough. I used the no fail 321 pie crust recipe that I have used since I was a kid. (Back then my mom got the recipe from Tupperware.) I did change a couple of measurements, but overall it is the same recipe. I can tell you it needs to be chilled at least 30 minutes, but if you leave it in the fridge overnight, like I did, you will really have to work it to roll it out.
  3. I found it easiest to cut the dough into rectangles and then cut them in half, by folding them over, to make sure that the top and bottom were the same size.
  4. Cut your dough, put it on the parchment, then fill it. My first recipe said to fill it, then transfer it. What was I thinking?
  5. Don’t put too much pudding in the middle. It will squeeze out when you crimp the edges, or leak out when it cooks. (About 1-2 T depending on the size of the square)
  6. Make sure you make small cuts in the top to vent the pastry, and when you press down the edges be sure that you are pressing through to the bottom so it doesn’t leak.

pudding pockets2I wanted these to be as authentic as possible, so of course they had to have glaze. You can opt to leave it off if you want, but it is super simple with Sugar 2.0 powdered sugar (You can find the recipe here) and water (Use 2 Tablespoons of powdered sugar and 3 teaspoons of water. Add sprinkles while wet, but allow the tops to dry before storing.) The sprinkles of course were just for some added flair, and my daughter is always asking for sprinkles and as we all know, sprinkles make everything better! You can also make them any size you want. I’m not very good at rolling out a beautiful long rectangle piece of dough so I probably cut out about three different sizes, and they all cooked the same! Whether you glaze and sprinkle, make them big or small, sit back, relax, and enjoy!

Chocolate hand pie pudding pockets using butter and sugar 2.0What treat is one of your favorite childhood memories?

What flavor of Hostess pies was your favorite?

Chocolate Pudding Pockets

By Angie Gouchenour

6-10 pockets depending on the size

pudding pockets5Ingredients


(321 dough)

  • 1 1/2 cups white wheat flour.
  • a pinch fine salt.
  • 1 Tablespoon Sugar 2.0
  • 8 tablespoons cold salted butter
  • 5-6 Tablespoons water (I used 5)


1 cup plant based milk (I used cashew)

2 Tablespoons corn starch

2 Tablespoons unsweetened cocoa powder

3 Tablespoons Sugar 2.0



Combine the flour, salt, and Sugar 2.0

Using a pastry cutter, knives, or a fork cut in the butter until there are pea size pieces

Using your hands knead in the water until it forms a ball

Wrap and chill for 30 minutes or longer


Combine the milk, corn starch, unsweetened cocoa powder, and Sugar 2.0

Stir to remove lumps and bring to a boil

Boil for 90 seconds

Remove from heat, cover and place in the fridge to cool

Assembly and Cooking

Preheat the oven to 400’f

On a lightly floured surface roll out half of the dough into a rectangle

Cut the dough into squares (See the notes above 3)

Place the squares on a parchment paper covered cookie sheet

Place a spoonful of chilled pudding in the middle of each square (See notes above 5)

Place a matching square of dough over the top and using a fork press down the sides all the way around (See notes above 6)

Cut 3 small slits in the top piece of dough

Bake in the oven for 10-12 minutes until the edges are light brown

Remove from the oven and place on cooling racks

Allow to cool completely before covering in glaze

8 thoughts on “Rookie Error – Chocolate Pudding Pockets

  1. Boy did I pick the wrong time to start my diet 😂 I love that you use Cashew Milk! We’re dairy free over here, so substitute recipes rock!

    Liked by 1 person

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