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Brown Sugar Tart Cookies

Featured in Treats That Make Everything Better.

Bake stuffed cookies with sweet cinnamon filling and a glaze. Ready in 90 minutes, including chilling. Makes 16 delicious tart-style treats.
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Clare Recipes
Updated on Fri, 25 Apr 2025 20:05:27 GMT
Brown Sugar Tart Cookies Pin it
Brown Sugar Tart Cookies | recipesclare.com

These brown sugar pop tart cookies bring back sweet childhood memories in every tasty bite. They blend the familiar taste of those classic brown sugar cinnamon breakfast pastries with soft, chewy cookies. When you break them open, you'll find a soft cake-like outside with a sticky, sweet cinnamon middle - it's a combo that makes regular cookies seem boring!

The first time I made these, childhood memories came flooding back. As soon as that sweet cinnamon smell filled up my kitchen, I knew they'd become a regular in my baking lineup. Watching my kids' excited faces when they discovered the gooey surprise inside made all the careful prep totally worth it.

Smart Ingredient Picks

  • Cake Flour: Get it fresh and measure it right for that melt-in-your-mouth softness. It's got less protein than regular flour, making your cookies extra tender
  • Unsalted Butter: Grab the good stuff with at least 82% fat content for the yummiest flavor and best cookie texture
  • Light Brown Sugar: Make sure it's soft without hard lumps so it mixes in smoothly
  • Ground Cinnamon: Don't skimp here - good quality cinnamon brings that authentic flavor you remember
  • Cornstarch: Check that it's fresh with no clumps to get that dreamy soft texture everyone loves

Mastering The Gooey Middle

Butter Basics:
Let your butter sit out until soft, then beat it until it's super fluffy. This puts air in the mix, setting you up for amazing cookie texture.
Making The Dough:
Mix sugars into the whipped butter bit by bit. Add eggs one after another, mixing until everything looks smooth and silky.
Handling Flour:
Gently fold in your dry stuff just until it's mixed in. Don't go crazy with mixing or you'll end up with tough cookies.
Creating Filling:
Roll the brown sugar-cinnamon mix into little balls that hold their shape when you wrap dough around them.
Putting It Together:
Wrap each filling ball completely in chilled dough. Roll between your hands until smooth, making sure no filling can escape.
Homemade Cinnamon Filled Cookie Treats Pin it
Homemade Cinnamon Filled Cookie Treats | recipesclare.com

While testing different methods, I found that popping the filled cookies in the fridge for just 15 more minutes makes them turn out so much better. My friend who's a pastry chef shared this trick, and it's been a total game-changer for getting that perfect texture every single time.

Tasty Pairing Suggestions

These cookies taste even better with a cold glass of milk or hot cup of coffee. Try making cookie ice cream sandwiches by putting vanilla ice cream between two cookies. For fancy dinner parties, arrange them on a plate with some fresh berries and a little caramel drizzle on top.

Fun Flavor Twists

Try mixing things up by adding some finely chopped nuts to your brown sugar filling or putting in a splash of maple extract for a fall feeling. Chocolate lovers can add cocoa to the dough and use chocolate filling instead. When you're celebrating something special, mix colorful sprinkles into the glaze on top.

Keeping Them Fresh

Store your cooled cookies in containers that seal tight, with wax paper between each layer so they don't stick together. They'll stay yummy for three days on your counter, or up to a week in your fridge. Want to make them way ahead? Freeze them without glaze for up to three months, then thaw and add glaze when you're ready to eat them.

After trying so many different versions, I've seen how these cookies bring happiness to everyone who tries them. There's something magical about that soft outside and gooey brown sugar inside. Whether you're remembering your childhood or making new memories, I've noticed these treats always get smiles around my table.

Freshly Baked Cinnamon Sugar Cookies Pin it
Freshly Baked Cinnamon Sugar Cookies | recipesclare.com

Frequently Asked Questions

→ How can I check if my butter's ready?
Leave butter out for about 1-2 hours so it feels cool but soft, around 60°F. Too warm? Your cookies might spread out too much.
→ Is freezing these cookies an option?
You sure can! Freeze them baked (skip the icing) for up to three months. Or freeze stuffed dough balls and bake straight from the freezer.
→ Why does the dough need chilling?
Chilling helps the dough keep its shape and makes filling it way easier. Dough stuck in the fridge too long? Let it sit out 30 minutes first.
→ What's the best way to store them?
Pop them into an airtight container. They'll last up to three days at room temp or a week in the fridge.
→ Can I try smaller cookies?
We recommend 1/4 cup size so the filling stays put. Going smaller might cause leaks while baking.

Brown Sugar Cookies

Soft brown sugar-filled cookies topped with a cinnamon glaze, reminiscent of classic pastries.

Prep Time
80 Minutes
Cook Time
10 Minutes
Total Time
90 Minutes

Category: Sweet Stuff

Difficulty: Intermediate

Cuisine: American

Yield: 16 Servings (16 cookies)

Dietary: Vegetarian

Ingredients

→ Cookie Base

01 2 eggs at room temp
02 1 teaspoon vanilla extract
03 3 3/4 cups of cake flour
04 2 tablespoons cornstarch
05 1 cup packed light brown sugar
06 1/2 cup white sugar
07 1 cup unsalted butter, softened
08 1 1/2 teaspoons baking powder
09 1 teaspoon kosher salt
10 1 teaspoon baking soda

→ Sweet Center

11 1 teaspoon cinnamon
12 3/4 cup light brown sugar, packed
13 5 tablespoons room temp butter
14 2 tablespoons of cake flour

→ Icing Drizzle

15 1 cup powdered sugar
16 3 tablespoons melted butter (let it cool)
17 1/2 teaspoon cinnamon
18 2 1/2 tablespoons milk

Instructions

Step 01

Pop the butter, white sugar, and brown sugar into your mixer bowl. Fit the paddle, then mix on high for 2-3 minutes. Pour in vanilla and crack in the eggs. Blend again for 1-2 minutes until it’s fluffy.

Step 02

In a separate bowl, whisk together the dry stuff. Dump it into the wet mix and stir on medium until just blended, pausing to scrape the sides if needed. Wrap and chill the dough for 1 hour.

Step 03

Set your oven to 350°F and toss some parchment paper onto two large baking trays.

Step 04

Grab a medium bowl. Mix the filling stuff together really well. Roll scoops (a heaping teaspoon’s worth) into balls and plop them on a tray.

Step 05

Scoop out 1/4 cup of chilled dough for each cookie. Split each one in two, then press a filling ball into the center of one part. Cover it with the second part, pinch the edges, and roll it into a neat ball.

Step 06

Space the cookie balls 2 inches apart on the sheets. Bake for 11-13 minutes, just until the edges look golden and the tops aren’t too puffy. Cool them on the tray for 5 minutes, then move them over to a cooling rack.

Step 07

Blend the glaze ingredients until smooth. Place parchment or wax paper under the rack, then drizzle each cookie with glaze. Leave them for 15 minutes to set before digging in.

Notes

  1. Butter should sit out for about 1-2 hours. It should feel cool, not warm (roughly 60°F).
  2. If the dough chills for longer than 1 hour, let it soften on the counter for 30 minutes before using.
  3. Store them in an airtight container at room temp for 3 days or pop them in the fridge for a week.

Tools You'll Need

  • A stand mixer or hand mixer with the paddle attachment
  • Two large baking trays
  • Parchment-lined paper
  • Wire racks for cooling
  • Measuring cup (1/4 cup)

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.
  • Uses dairy (butter)
  • Eggs included
  • Contains wheat/gluten

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.
  • Calories: 420
  • Total Fat: 18 g
  • Total Carbohydrate: 61 g
  • Protein: 5 g