Loaded Oatmeal Sandwich Cookies

I love cookies! I’ve been on some sort of cookie binge lately, searching for that old school Americana feeling of stepping into a house warmed with the scent of freshly baked cookies. It makes me feel like I’m not an adult of 31 with worries that didn’t concern boys, homework or prom. I miss that. When we’re young, we want to grow up as fast as we can, take for granted how easy life can be. Now that I’m staring 32 in the eyes, I can’t help but wish I were 12 again!

I made homemade oatmeal cookie sandwiches this past weekend after seeing this post on Annie’s Eats for moon pies. I know moon pies are more of a east coast thing, growing up in Oakland, I loved the west coast version, It’s It, vanilla ice cream sandwiched between oatmeal cookies and dipped in chocolate. A bit different from the east coast oatmeal cookies with marshmallow cream dipped in chocolate, but still delicious regardless. I modeled my cookie sandwich after the It’s It more than the moon pie, using a vanilla frosting vs marshmallow cream. I also felt cookies and frosting alone were already sweet enough so I didn’t feel the need to dip or drizzle it with dark chocolate.

I used the oatmeal recipe on Annie’s site, but changed it a bit since she said her cookies were a bit crisp. I love moist chewy oatmeal cookies, so I changed the recipe around, substituted some ingredients, added new ingredients and changed the cooking time. The result were moist and chewy near perfect cookies! As for the frosting, I found this recipe for “That’s The Best Frosting I’ve Ever Had” months ago, I’ve used it several times and loved it, its my go to frosting recipe, you have to try it! Its a bit strange, but trust me, it’s wonderful, warning, the recipe makes quite a bit of frosting, I halved the recipe and had enough to make about 14 cookie sandwiches.

Makes 36 Loaded Oatmeal Cookies or 18 Cookie Sandwiches


For Cookies
1 cup All Purpose Flour
3/4 tsp Baking Powder
1 tsp Baking Soda
1/2 tsp Salt
1 tsp Ground Cinnamon
1 1/2 Stick Unsalted Butter, soften (or 12 tbsp)
1 Egg, room temperature
1 cup Brown Sugar, packed (preferably dark brown sugar)
2 tsp Vanilla Extract
2 1/4 cup Rolled Oats
1 cup Dried Cranberries
1 cup Almonds, toasted and roughly chopped
1 cup Dark Chocolate Chips

For Filling
5 tbsp All Purpose Flour
1 cup Milk
1 tsp Vanilla Extract
1 cup Unsalted Butter, soften
1 cup Granulated Sugar


For Cookies
1. Preheat oven to 325 degrees
2. In a sheet pan, toast whole almonds in the oven for about 10mins or until they are fragrant. Roughly chop and set aside to cool
3. Whisk together flour, baking powder, baking soda, salt and cinnamon in a bowl and set aside
4. In a large bowl, using a hand mixer, cream together butter and brown sugar until fluffy and sugar has dissolved, about 3mins. Blend in egg and vanilla
5. Add flour mixture and mix until just combined. Using a spatula fold in cranberries, oats, chocolate chips and cooled almonds into the batter
6. Scoop about 2tbsp of dough onto cookie sheet about 2 inches apart. Bake for exactly 14mins, rotating pan halfway through
7. Allow to cool on sheet for about 5mins before moving to wire rack to cool completely.

For Filling
1. In a small saucepan, whisk together flour and milk. Continue to whisk while heating until thickens to the consistency of a browned batter
2. Remove from heat and allow to cool until room temperature then stir in vanilla extract. Must be completely cool before using it in the next step
3. In a large bowl, using a hand mixer, cream butter and sugar together until smooth, make sure sugar is fully dissolved, you don’t want any graininess left
4. Add cooled flour/milk/vanilla mixture to sugar mixture and beat on medium high until smooth and fluffy. If it looks separated, you haven’t beaten it enough. End product will resemble whipped cream.

Assembling Cookie Sandwiches

1. Take 2 completely cooled oatmeal cookies that are about the same size and add a big dollop of frosting in the middle of the flat side of the cookies
2. Smush cookies together until frosting reaches the edges
3. Wrap and refrigerate at least 5 hours to allow frosting to slightly harden
4. Store in the refrigerator

1. Lightly toasting the nuts brings out their essential oils and makes them taste better.
2. Don’t over mix the flour into the creamed butter and sugar mixture. I like to mix until just combined with some streaks of flour left, then fold in the rest of the ingredients. Keeps the cookies from being tough
3. Use a cookie scoop to insure you have the same amount of dough in each cookie. It also promotes even cooking
4. Make sure cookies are completely. cool before adding frosting.

The cookies are incredibly moist and chewy with hints of tartness from the dried cranberries and decadence of slightly melted dark chocolates chips. The frosting is lightly sweetened but ethereally fluffy, like whipped cream, it melts in your mouth as soon as it touches your tongue
I couldn’t help myself and indulged in a cookie or two while making the frosting, then barely able to wait the 5 hours before munching on a few cookie sandwiches. I store them in the refrigerator, I let them rest on the counter top for about 5mins before serving, just to take the chill off of them. Lasts 2 weeks in the fridge or 4 days in my household.

Posted from Ms Fatty’s BlackBerry 😉

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