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Preheat the oven to 350 degrees F. Line two large baking sheets with parchment paper.
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In a medium mixing bowl whisk together the flour, oats, baking soda, salt, and cinnamon.
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In the bowl of a stand mixer fitted with the paddle attachment, beat the butter on medium speed until light and fluffy. Add the sugars and beat another 2-3 minutes until fully incorporated.
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Scrape down the sides, add the egg, and vanilla. Mix on medium until combined.
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Add the dry ingredients and mix on low until just about combined. Add the raisins and chocolate. Mix to combine on low.
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Using about a 1/4 cup scoop, portions out balls of dough, about 6 per baking sheet.
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Bake cookies for 10-12 minutes until sides are ever so slightly golden and the middles still look soft. Let the cookies cool on a baking sheet for 5 minutes and then transfer to a wire rack to cool completely.