Mini Apple Pie Cinnamon Sugar Cookie Cups

September 29, 2022

For something that’s as tasty as it is cute, fall is the perfect time to serve mini apple pies. These feature a spiced stovetop filling piled high into bite-sized cinnamon sugar cookie cups.

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Usually when I’m baking, the main goal is flavor. However, with these, it was all about how adorable they could be — and flavor. We’re not about to sacrifice taste just for cuteness. But having both? Total bonus, especially when you are looking for a fun treat to serve at all those upcoming fall events.

I decided to stay fairly traditional here with the apple pie filling, and make the cookie dough a place for changing it up. These are based on a cutout cookie dough, so they are nice and sturdy for the filling. But the addition of the spice from the cinnamon and the soft melt-in-your-mouth shortbread texture make a perfect trifecta.

What You Need to Get Started

You can easily find all of the ingredients for these apple pie cinnamon sugar cookie cups at your grocery store:

Pantry: Sugar, Flour, Cornstarch, Brown sugar
Spice Rack: Cinnamon, Salt, Apple pie spice (or pumpkin pie spice, or any combination of ginger, cloves, allspice, and nutmeg)
Fridge: Butter, Eggs
Produce: Apples
Equipment: Stand mixer or hand mixer, Whisk, Parchment paper, Rolling pin, Cupcake pan, Cooling rack, Saucepan, Flexible spatula

Let’s Make Cinnamon Sugar Cookie Cups

When you are using cookies as pie crust, the dough needs to be sturdy enough to stand up to the filling, soft enough so the first bite doesn’t cause any large cracks, and tasty enough that you want to keep eating that cookie.

That’s why I decided to go with a modified shortbread-based cutout cookie crust, which includes cornstarch for extra softness. Plus, there’s the added bonus of these cinnamon sugar cookie cups tasting extra buttery, kind of like a pie crust would.

Begin the Cookie Dough

To get started, you’ll first want to combine the cinnamon and sugar together, and then cream both with the butter. So let’s get started by mixing the cinnamon into the sugar until it’s distributed throughout.

You’ll be using cold butter in this recipe, which eliminates any need for chilling the dough, and will help the cookies hold their shape while baking. Butter from the fridge will work the best, since it will be difficult to cut into cubes if it’s frozen.

Add these butter bits into a large mixer bowl, and be sure your stand mixer is fitted with the paddle attachment. If you only have access to a hand mixer, use the beaters and a large, deep bowl to make this dough.

Pour the cinnamon sugar into the bowl with the butter, and mix on a low speed until everything is incorporated together and the butter begins to look a bit fluffy, about three minutes. Then mix in the eggs as well.

Finish Mixing the Dough

Meanwhile, you can prepare the remaining dry ingredients. Use a medium to large mixing bowl, and add in the flour, cornstarch, and salt. Using cornstarch is not optional here, since it really does make the texture of these cookies cups absolutely perfect and soft.

Whisk these dry ingredients together, then add them into the mixer bowl with the creamed butter and sugar and a little bit of water (or apple cider!). Use a spatula or the paddle attachment to begin mixing the flour into the butter by hand before turning on the mixer. Otherwise, you may end up with flour everywhere!

Then continue mixing on low speed until it begins to form into dough and there are no longer large streaks or pockets of flour, about three or four minutes. When it’s ready, the cookie dough will be dry, not sticky, but will hold together without crumbling.

Roll and Shape the Cookies

Work with only about a third to half the dough at a time, and roll it into a disc shape. Place that between two large pieces of parchment paper on a flat working surface. Then, use your rolling pin on top of the parchment to roll out the dough until it’s between an eighth and a quarter inch thick.

Grab a large circle cookie cutter that’s around three inches in diameter. If you don’t have one, you can use the rim of a bowl instead to give you a guideline, and then a paring knife to finish cutting out the shape.

Either way, hang on to that paring knife. You’ll want to use it to cut out four triangular notches in each cut out circle. These don’t need to be perfect, but these notches will help you shape the dough into the cup shape without having a lot of excess.

The good news about this cookie dough is that you can put all the scraps in a pile and then roll it out again to create more circle cutouts. Into each of those, you guessed it, use your paring knife to cut the four notches. If you have a little extra dough, don’t worry, we can use that later on!

As you go, place the cookie dough cutouts into a nonstick cupcake pan. I found it easier to shape the cups first, by bending up the edges of the cookie and gently pressing the sides of the notches together.

Then you can add each of these into one of the cups of the cupcake pan. Use a toothpick or fork to add a few small holes in the bottom of each cookie cup. This will help prevent excess puffing up when they bake.

If you’d like, you can also pinch the edges of the cookie cups with your finger tips to create a scalloped pie crust-like edge. However, that’s totally optional, and these will be delicious even without it.

Bake and Cool the Cookie Cups

Bake the cookie cups for right around nine minutes, until they appear dried out on the edges. They will not have browned up too much. Let them cool in the pan for ten minutes, and then transfer them to a wire rack to cool completely.

If the cookie cups are not releasing easily from the pan, give them a gentle nudge by pressing against the walls of the cookie cup to rotate it slightly. This should allow the bottom to release, and the cup will slip right out.

How to Make Apple Pie Filling

While the cinnamon sugar cookie cups are cooling, it’s time to make the apple pie filling! Get started by prepping your apples. Firm and sweet apples work best here, like Gala, Braeburn, or Honeycrisp, nothing too tart. I would also avoid very soft apples in this recipe, since they may just turn to mush when cooked.

Dice the apples into quarter-inch cubes, and then add all of these to a large saucepan.

I used six small apples to get six cups of chopped fruit, but every apple is different. While cutting, definitely keep an eye on how much you have by using a measuring cup to make sure you are on the right pace.

Cook the Apple Pie Filling

Add the chopped apple pieces along with butter, brown sugar, cinnamon, and some apple pie spice into a large saucepan. Begin cooking this over medium heat, stirring frequently until the butter melts and the sugar begins to dissolve into the liquid the apples are releasing.

If you don’t have apple pie spice, pumpkin pie spice will also work well here. Or you can make your own by combining equal parts cloves, ginger, allspice, and nutmeg. If you prefer one of the spices over another, feel free to adjust that balance to your liking.

Cover the pan and allow the apples to soften for right around ten minutes. After every two minutes or so, uncover and give them a good stir. When the apples have softened (try one to check) and the liquid is thick and syrupy, your filling is ready to go.

If the apples are soft but the syrup hasn’t thickened yet, you can continue to cook the filling uncovered for an additional few minutes. This will help remove any excess water, which can happen depending on the apples you use.

Set the pan with the apple filling aside for a few minutes to allow it to cool slightly before filling the cups.

Once both the cookies and the filling have cooled, add about a tablespoon-and-a-half of the filling into each cup. It’s okay if these measurements aren’t exact. Mine were pretty heaping, I’ll admit. If you have some extra filling, just top off any cups that are looking a little sparse.

Add a Lattice Top

These are ready to serve now, but it’s more fun if you add a lattice or other topping! To make the lattice, you’ll need to have some excess cookie dough. You probably ended up with a little bit leftover after cutting out the last cookie.

This will be enough to make a few lattices, but not to top all your cookies. If you want them all to have a lattice top, be sure to set aside one whole cookie’s worth of dough.

Roll out this extra dough a little bit thinner than you did for the cookie cups themselves. The shape doesn’t matter too much here, since next you will be using a paring knife to cut the dough into thin strips.

Start by using the longest strips to make a plus in the middle of each mini cookie pie. Then, weave the shorter strips in between, creating an over-under pattern. These are pretty small, so you can also cheat the lattice a little bit by simply laying pieces perpendicular to one another without weaving.

Since the lattices are made with raw dough, you will need to bake these again. You can place the cookie cups back in the cupcake pan and then bake them with the lattices for an additional five minutes or so, just until those strips appear dry.

Be sure to let these cool for a couple minutes before serving them.

Making These in Advance

If you are planning ahead, you are in luck with these! The cookies are the best piece to make far in advance, since they can be stored at room temperature for a few days in an airtight container. Once fully cooled, they can even be gently stacked to save space, if needed. But they can also be frozen for a few months. Just let them thaw overnight.

The cooked apple pie filling can also be made ahead and can then be stored in a sealed container in the fridge for a few days. Reheat this filling on the stove to serve these mini pies warm, or at least let the filling sit at room temperature.

As for the finished and filled cookie cups, these can be stored in a tightly sealed container at room temperature for a couple days. If you top these with any sort of sugar or sprinkle, it will likely dissolve into the filling after a few hours sitting out, so keep that in mind. The lattices should hold up as well as the cookies themselves.

What’s better than an apple pie? A mini one that you don’t have to share! Especially when the crust is actually a cinnamon sugar cookie cup.

How to Serve Apple Pie Cookie Cups

One of my favorite parts of these cinnamon sugar cookie cups is that there are so many different ways you can top them, not just the cookie lattice! Try drizzling a few with homemade caramel or butterscotch sauce, or even some local honey.

You could also top each one with a mini scoop of ice cream (like coffee!) or homemade whipped cream. Try using a melon baller to help you get a smooth shape in the smaller size. Beyond that, there’s seasonal sprinkles, sparkling sugar, pearl sugar, or anything else that you can think of!

And while these are super cute on their own, they can also be part of a fun cookie spread or exchange. Try serving them alongside some other fun favorites, like blueberry cheesecake cookies, plum jam newton-style cookies, peanut butter cookies bars, and pecan, fig, and chocolate chip oatmeal cookies.

More Apple Recipes to Try

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