Rolo Sugar Cookie Cups are soft, sweet, and irresistibly indulgent. They’re perfect for sharing, gifting, or savouring slowly.

Each cup features a tender sugar cookie base that melts in your mouth.

A warm Rolo candy nestled in the center creates a rich caramel surprise.

The combination of buttery cookie and gooey chocolate caramel is pure comfort.

Every bite delivers a perfect balance of sweetness and texture.

Printable Recipe Card with a Full List of Ingredients and Instructions is Located at the Bottom of the Post.

Be sure to read through the entire post so that you don’t miss out on any important tips and tricks!

To start making Rolo Sugar Cookie Cups I dumped some butter and granulated sugar into a large mixing bowl.

Then I used an electric hand mixer to cream them together.

After this I added in an egg plus a bit of vanilla extract,  and beat again with the electric hand mixer. 

Next I added in some Bob’s Red Mill 1 to 1 Gluten Free Baking Flour, baking powder and a bit of salt.

To mix in the last bit of flour I used a large wooden spoon.

Then I greased a mini muffin tin.

Using a 1 tablespoon scoop I filled each muffin cup with the cookie dough.

Then I baked the cookie dough in a preheated 350F oven for 10 – 12 minutes.

While the cookies were baking I unwrapped the Rolo Candies.

After 10 – 12 minutes I removed the pan from the oven.

I immediately pressed a Rolo candy into the centre of each hot cookie to form the cookie cups.

The caramel adds a silky smooth contrast to the delicate cookie crumb.

These treats are rich without being overwhelming.

They look charming and bakery-worthy with minimal effort.

Gluten free Rolo Sugar Cookie Cups are a simple treat that tastes wonderfully indulgent.

Printable Recipe Card with a Full List of Ingredients and Instructions is Located at the Bottom of the Post.

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PRINTABLE VERSION OF THE RECIPE CAN BE FOUND AT THE BOTTOM OF THE PAGE

Ingredients You’ll Need to Make these Rolo Sugar Cookie Cups:

• 1/2 cup + 2 tbsp butter, softened
• 3/4 cup granulated sugar
• 1 egg, large
• 1/2 tsp vanilla extract
• 1  3/4  cups Bob’s Red Mill 1 to 1 Gluten Free Baking Flour
• 1 tsp baking powder
• 1/8 tsp salt
• 24 Rolo candies

How to Make Rolo Sugar Cookie Cups:

1. Preheat oven to 350F and grease a mini muffin tin.  
2. Dump butter and granulated sugar into a large mixing bowl. Use an electric hand mixer to cream them together on medium speed.
3. Add the egg and vanilla extract.  Beat again on medium speed to combine.
4. Measure in the Bob’s Red Mill 1 to 1 Gluten Free Baking Flour, baking powder and salt.
5. Use the electric hand mixer on low speed until the dry ingredients have been incorporated into the dough. Finish combining with a large wooden spoon.
6. Use a 1 tablespoon scoop to transfer the cookie dough into the muffin pan.
7. Bake in the preheated 350F oven for about 10 – 12 minutes.
8. While cookies baking unwrap the Rolo candies.
9. As soon as cookies are removed from the oven press a Rolo candy into the centre of each one.
10. Allow cookie cups to cool.
11. Remove from muffin pan once cooled.
12. Serve and enjoy!

FAQs:

How do I store Rolo sugar cookie cups?

Rolo sugar cookie cups can be stored a few different ways depending on how long you’d like to keep them fresh:

1. At room temperature (short-term):
Place the cookie cups in an airtight container.
Separate layers with parchment or wax paper so the caramel centers don’t stick together.
Store in a cool, dry spot for up to 3 days.

2. In the fridge (medium-term):
Keep them in an airtight container lined with parchment paper.
This helps prevent condensation from softening the cookie base.
They’ll stay fresh for about 5–7 days.

3. In the freezer (long-term):
Freeze the cookie cups in a single layer on a baking sheet until solid, about 1 hour.
Transfer to a freezer-safe container or bag, separating layers with parchment paper.
Freeze for up to 2–3 months.
When ready to enjoy, thaw at room temperature for 20–30 minutes before serving.