A little retro, but definitely a classic, these gluten free oatmeal raisin sandwich cookies are perfect for those with gluten sensitivities.
I consider it one of my callings in life to feed everyone. You come to my house, you get fed at least 75% of the time. The percentage is a little low at the moment because life. So let’s talk about what it takes to be a good “feeder”. Part of feeding the world means one keep tabs on people’s preferences, allergies, etc. It may take me a bit to remember someone’s name, but I’ll remember their aunt’s sesame allergy and that they don’t like raw onions in their salad almost instantly. I don’t know if it’s necessarily a useful “talent” in the grand scheme of things, but that’s sort of how these cookies happened.
You see, I have a few friends who don’t handle gluten well and I like to bake for them, which is why you see me testing gluten free things and why gluten free recipes will continue to appear from time to time on the blog.
One day I was doing some shopping and passed an end cap display of the Little Debbie’s snacks or whatever brand makes an oatmeal sandwich cookie. And my immediate thought was, “I should make some gluten free oatmeal sandwich cookies”. So I did, and I shared them with two friends, and they liked them, so they’re on the blog.
Sometimes we have fancy stories for recipes, and sometimes there’s no story at all. It’s just a recipe idea I wanted to play with that turned out well.
A few quick things about these cookies. They are thicker because I didn’t smush them after scooping out the dough. Feel free to flatten a bit for a thinner cookie, but bake for to 4-7 minutes to avoid over baking. I would err on the side of slightly under-baking the cookie since they do need to set on the pan for a few minutes before moving, and gluten-free goods are easily over-baked.
I hope you enjoy these cookies! My husband said he couldn’t guess they were gluten free (hooray) and thought they paired perfectly with milk. I agree. 😉

Gluten Free Oatmeal Raisin Sandwich Cookies
Ingredients
Cookie Batter
- 8 tbsp unsalted butter, softened
- 1/2 cup packed brown sugar
- 1 egg
- 1 tsp vanilla extract
- 1 cup gluten free all-purpose flour
- 1/2 tsp salt
- 1/2 tsp baking soda
- 1/2 tsp baking powder
- 1 1/4 cups gluten free rolled oats
- 1/2 cup raisins
Cinnamon Cookie Filling
- 2 tbsp butter, softened
- 2 tbsp coconut oil
- 1 cup powdered sugar
- 1 tsp ground cinnamon
Instructions
- Preheat the oven to 375 F, line 2 baking sheets with parchment paper and set aside.
- Cream the butter and sugar in the bowl of a stand mixer or in a mixing bowl using a hand mixer on medium speed until light and fluffy, 1-2 minutes.
- Add the egg and vanilla extract
- Stir together the flour, salt, baking soda, and baking powder in another bowl, then add to the butter and sugar mixture.
- Stir in the oats and raisins.
- Use a 1 tbsp sized cookie scoop (small size) to scoop the cookies onto your baking sheet. Press slightly to flatten.
- Bake 6-8 minutes until the cookies have a very light golden coloring along the bottom edge, rotating the pans once during baking. Remove from the oven and allow to set on the pan for 2-3 minutes before removing to a wire rack to cool completely while you prepare the filling.
- Prepare the filling by beating together the coconut oil and butter until combined, then stirring in the powdered sugar and cinnamon. Place into a piping bag with the tip cut off and pipe onto one cookie, then top with another to make your sandwich.
- Store in an airtight container up to a week.