Brown Sugar Oatmeal Cookie Cups

Inspired by classic Oatmeal Creme Pies, these cookie cups are made in a mini muffin tin for a bite-sized dessert that packs a sweet, brown sugar punch.

The past few weeks have looked something like this. Cook, bake, photograph, wash 400 dishes. Repeat.

Between work and this blog and a few new freelance projects, the Inquiring Chef kitchen is buzzing, and both Frank and I need a vacation.

Or at least to order a pizza and sit on the couch.

Or to have the two year olds make us a pizza. Kids learning to cook is pretty much the best thing ever. Though there’s no sense in trying to get them to understand that pizzas get soggy when piled high with pesto + marinara + olive oil + 3 kinds of cheese.

Fortunately, even two-year-old pizza creations, piled high, taste awesome.

Brown Sugar Oatmeal Cookie Dough

But as you can see, there’s no pizza around here today. Today we have a dessert that has been at least a year in the making. At some point, Frank started talking about an oatmeal version of our well-loved cookie cups that would be topped with rich, creamy frosting. I knew right away that the flavors he had in mind were those of Oatmeal Creme Pies. And because he so rarely makes such a specific request, I knew I had to deliver.

Months and many test batches of these little bites later, we found the one. To get the flavor and texture close to the soft/chewy combo in creme pies, the key turned out to be using all brown sugar in the cookie dough. Not as intense as the molasses used in original creme pies, the nutty, caramel flavor is there. And it’s lovely.

Cream Cheese Frosting

On top is a super basic cream cheese frosting with a hint of vanilla. In truth, it barely qualifies as “frosting”. It’s really a cream. But cream cheese “cream” doesn’t really work, so frosting is what we will call it. This version is super thick, lightly sweet, and can be easily made ahead. I don’t get too fussy with it, as you can see. I just mix it in a standing mixer, spoon it into a plastic bag with the tip cut off and squeeze it on top of the bites

These cookie cups can be easily made ahead, stored at room temperature for 3 days and will still be soft and tender. The frosting can be made 3 days ahead as well and stored, in the plastic bag, in the fridge. If you’re taking them to go, just bring the elements and pipe the frosting (cream) on right before serving.

And if you’re looking for a little something extra, finish them with a sprinkle of rolled oats and a drizzle of caramel sauce.

Just don’t leave that caramel sauce around and expect it to stay looking all nice for photos.

Little fingers will find it.

Print Recipe

5 from 3 votes

Brown Sugar Oatmeal Cookie Cups

These bite-sized oatmeal cookie cups are a fun twist on everything that is good about classic oatmeal cookie sandwiches. Made with brown sugar these treats are super tender and have a rich, caramel flavor.

Prep Time30 mins

Cook Time10 mins

Total Time40 mins

Course: Dessert

Servings: 35 mini cookie cups

Author: Jess Smith via Inquiring Chef

Ingredients

For the Oatmeal Cookie Cups:

• 1/2 cup (1 stick) Butter, softened
• 1 cup packed Brown Sugar
• 1 tsp Vanilla Extract
• 1 large Egg
• 3/4 cup All-Purpose Flour
• 1/2 tsp Salt
• 1/2 tsp Baking Soda
• 1 1/4 cups Oats ("old-fashioned" or "rolled")

For the Cream Cheese Frosting:

• 8 oz. Cream Cheese, softened
• 1/2 cup Powdered Sugar
• 1 Tbsp Milk
• 1/2 tsp Vanilla Extract

Optional Toppings:

• 1/4 cup Caramel Sauce (I just use store-bought)
• 1/4 cup Oats ("old-fashioned" or "rolled")

Instructions

• Preheat oven to 350 F. Spray a mini muffin tin with nonstick cooking spray.
• Beat together butter and brown sugar until light and fluffy. Beat in vanilla and egg until well combined.
• In another bowl, stir together flour, salt and baking soda. Add dry ingredients in 2 batches, mixing just until combined. Add oats and mix jus until oats are evenly incorporated.
• Working with a heaping tablespoon of dough at a time, roll into balls and place in the holes of the muffin tin.
• Bake until the edges of the cookie cups are firm and just beginning to brown (the centers should still look soft), 10 to 12 minutes. Let cookie cups cool completely in the muffin tin before removing. Trust me on this - they are very tender and may crumble if you remove them before they are cool. (Note: the centers of the cookie cups will sink as they cool. This provides the perfect spot for creamy frosting!)
• When cookie cups are cool, make frosting by beating together cream cheese, powdered sugar, milk and vanilla extract until smooth. Add milk a bit more at a time, if needed to bring the mixture together, but you want it to be quite thick. Spoon frosting into a piping bag or Ziploc bag. Clip the end off and pipe frosting into each of the cookie cups.
• If you'd like, top the cookie cups with caramel sauce and a sprinkling of oats just before serving.
• Store the cookie cups in a sealed container at room temperature for up to 3 days. Fill and top just before serving.

When they’re not sneaking caramel sauce straight out of my photo shoot, Molly and Clara can be found lounging in the backyard, in outfits they selected entirely themselves, teaching the dolls to “relax”.