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Homemade Oatmeal Cream Pies with Creamy Vanilla Filling

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These homemade oatmeal cream pies are chewy cookies with hints of cinnamon, brown sugar, and vanilla, sandwiched around a creamy, not-too-sweet filling. They are a homemade version of the classic oatmeal cream pie, perfect for sharing or enjoying as a sweet treat.

  • Total Time: 1 hour 30 minutes
  • Yield: 16 sandwiches

Ingredients

Scale

Oatmeal Cookies

  • 1 cup unsalted butter (226 grams), softened
  • 1 cup brown sugar (200 grams), packed
  • 1/2 cup granulated sugar (100 grams)
  • 1 tablespoon molasses
  • 2 teaspoons vanilla extract
  • 2 large eggs
  • 2 cups all-purpose flour (250 grams)
  • 1/2 teaspoon cinnamon
  • 1 teaspoon baking soda
  • 1/4 teaspoon salt
  • 3 cups quick oats

Cream Filling

  • 3/4 cup unsalted butter (168 grams), softened
  • 2 ounces cream cheese (57 grams), full-fat brick style
  • 3โ€“4 cups powdered sugar (330โ€“440 grams)
  • 1 teaspoon vanilla extract
  • 1/4 teaspoon salt
  • 1 tablespoon cream, if needed

Instructions

Oatmeal Cookies

  1. Preheat the oven to 350ยฐF (180ยฐC or 170ยฐC fan-forced). Line cookie sheets with silicone baking mats or baking paper.
  2. In a large bowl, beat the butter, brown sugar, and granulated sugar together until fluffy.
  3. Mix in the molasses, vanilla extract, and eggs until creamy.
  4. Turn off the mixer and add the flour, cinnamon, baking soda, and salt. Stir a few times by hand, then mix on low speed until incorporated.
  5. Stir in the oats.
  6. Form the dough into balls about 1 to 1 1/2 tablespoons in size. Place them 2 inches apart on the prepared cookie sheets. The recipe typically makes about 32โ€“34 cookies, enough for 16โ€“17 sandwiches.
  7. Bake one sheet at a time in the middle of the preheated oven for about 9โ€“11 minutes, or until the tops look set.
  8. Cool the cookies on the baking sheet for at least 10 minutes before transferring them to a wire rack to cool completely.

Cream Filling

  1. In a large bowl, beat the butter until fluffy.
  2. Cut the cream cheese into 3โ€“4 pieces and beat it into the butter.
  3. Add 1 1/2 cups powdered sugar, vanilla, and salt. Start mixing on low speed, then gradually increase to medium until combined.
  4. Beat in the remaining powdered sugar about 1/2 cup at a time until the desired sweetness is reached. If the frosting is too thick, beat in 1 tablespoon of cream.

Assemble the Cookies

  1. Spread about 1 to 1 1/2 tablespoons of frosting onto the bottom of one completely cooled cookie.
  2. Place a second cookie on top, with its bottom facing down, to make a sandwich. Repeat with the remaining cookies and filling.

Notes

  1. Smaller batch: Divide the recipe in half to make a smaller batch.
  2. Molasses: Molasses adds the classic oatmeal cream pie flavor. Honey can be substituted if needed.
  3. Flour: Measure carefully to help prevent dry cookies. Whisk the flour, spoon it into a dry measuring cup, and level the top, or use a kitchen scale.
  4. Oats: Quick oats are preferred, but rolled oats can also be used.
  5. Cream cheese: Replace the cream cheese with additional butter if preferred.
  6. Make ahead: Bake the cookies 1โ€“2 days ahead, cool completely, and store at room temperature in an airtight container. Cookies can also be frozen for up to 2 months in an airtight container. Thaw in the refrigerator and frost when ready to serve.
  7. Storage: Store assembled cream pies in an airtight container at room temperature for up to 3 days or in the refrigerator for up to 5 days.
  8. Nutrition: Nutrition information is an estimate based on one cookie and the recipe yielding 16 equal-sized servings with all the frosting used.
  • Author: Emma
  • Prep Time: 1 hour
  • Cook Time: 10 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American