
These brown sugar pop tart cookies pack childhood memories into every tasty bite. They blend the yummy flavors of traditional brown sugar cinnamon pop tarts with the comfort of soft cookies. When you bite in, you'll find a soft, cake-like outside covering a gooey brown sugar-cinnamon middle, making a treat that's way better than your average cookie.
The first time I made these cookies, childhood memories came flooding back. As that sweet brown sugar-cinnamon smell filled up my kitchen, I knew right away they'd become one of my go-to recipes. Seeing my kids' excited faces when they found the sweet surprise inside made all the careful prep totally worth it.
Smart Ingredient Choices
- Cake Flour: Make sure it's fresh and measured right to get that soft, tender bite. It's got less protein than regular flour, which is why these cookies turn out so soft
- Unsalted Butter: Go for good quality with at least 82% fat content to make these cookies taste rich and feel just right
- Light Brown Sugar: Check that it's soft and lump-free so it mixes in smoothly
- Ground Cinnamon: Don't skimp here - get the fragrant, good stuff for that real pop tart taste
- Cornstarch: This needs to be fresh without clumps to help make your cookies wonderfully soft
Mastering Those Gooey Middles
- Getting Butter Just Right:
- Use butter that's softened to room temp and beat until it's fluffy and light. This puts air in the mix, which is key for getting the texture spot-on.
- Making Your Dough:
- Mix in your sugars bit by bit into the whipped butter, waiting until each addition disappears. Put eggs in one at a time and mix until everything looks smooth like silk.
- Adding Dry Stuff:
- Gently fold in your measured flour mixture, stopping as soon as it's mixed in. If you work it too much, your cookies won't be soft, so go easy here.
- Creating The Filling:
- Press the brown sugar-cinnamon mix into little firm balls. They should hold their shape when you wrap dough around them.
- Putting It All Together:
- Wrap chilled dough completely around each filling ball, making sure the edges are sealed tight. Roll between your hands until smooth so no filling can escape.

During my kitchen tests, I found out that cooling the filled cookies for just 15 more minutes makes a huge difference in how they turn out. I learned this quick trick from my friend who's a pastry chef, and it's really improved how these cookies come out every single time.
Tasty Pairing Suggestions
Make these cookies even better by having them with cold milk or hot coffee. Try making little ice cream sandwiches by putting vanilla ice cream between two cookies. For fancy get-togethers, lay them out on a plate with some fresh berries and drizzle caramel sauce over everything.
Fun Flavor Twists
Try changing up the filling by mixing small chopped nuts into the brown sugar or adding a bit of maple extract for a fall flavor. Chocolate fans can add cocoa to the dough and use chocolate filling instead. When you're celebrating something special, put colorful sprinkles in the glaze to make them festive.
Keeping Them Fresh
After they cool, put your cookies in a container that seals tight, with wax paper between each layer so they look nice. They'll stay good on your counter for three days, or keep them in your fridge for up to a week. If you need them to last longer, freeze them without glaze for up to three months, then thaw and add glaze when you're ready to eat them.
After making batch after batch, I've found these cookies bring happiness to everyone who tries them. That soft outside with the gooey brown sugar inside creates something really special. Whether you're thinking back to your childhood or making new memories, these cookies always bring smiles to everyone at my table.

Frequently Asked Questions
- → What’s the best way to check butter temp?
- Butter should feel cool but not hard, about 60°F. Let it sit out for 1-2 hours max. Too soft and your cookies might spread too much.
- → Can I keep these cookies in the freezer?
- Sure! Store baked cookies without icing for up to 3 months. Or freeze dough balls and bake them straight from the freezer.
- → Why chill the dough before baking?
- Cold dough reduces spreading and makes stuffing the cookies less messy. If they sit longer than an hour in the fridge, soften for 30 mins first.
- → What’s the best way to store them?
- Keep them in a sealed container on the counter for 3 days, or toss them in the fridge for up to a week.
- → Can I make smaller cookies instead?
- It’s better to stick with the 1/4 cup portion to hold in the filling properly. Smaller ones might leak when baking.