Preheat oven to 350°F (175°C). Line two baking sheets with parchment paper. Set aside
In a large bowl using a hand or stand mixer fitted with the paddle attachment, cream together the butter, brown sugar, and granulated sugar on medium speed for 2–3 minutes until light and fluffy.
¾ cup unsalted butter, ½ cup brown sugar, ½ cup granulated sugar
With a rubber spatula, scrape down the sides and bottom of the bowl. Add the egg and beat on medium-low speed until fully incorporated and smooth.
1 large egg
All at once, add the the flour, cornstarch, oats, cinnamon, nutmeg, baking powder, and salt. Mixing on low speed until just combined. Do not overmix.
Lightly mash the berries with a potato masher or spoon to release some juice.
Bring to a simmer over medium heat, stirring frequently to avoid burning.
Simmer for 20–25 minutes until thickened and jammy, stirring occasionally.
If desired, blend briefly with an immersion blender for a smoother texture or strain to reduce seeds.
Let cool slightly. Transfer to a container and refrigerate until ready to use (up to 2 weeks).
Make the Cinnamon Streusel:
Preheat oven to 400°F (205°C). Line a small baking sheet with parchment paper.
In a medium bowl, mix the brown sugar, flour, oats, cinnamon, and salt. Cut in the cold butter using a fork or your fingers until the mixture forms small clumps.
¼ cup light brown sugar, ⅔ cup all-purpose flour, 1 teaspoon ground cinnamon, Pinch of salt, 4 tablespoons unsalted butter, 3 tablespoons rolled oats
Spread evenly on the prepared sheet and bake for 8–10 minutes, stirring halfway through, until lightly golden.
Cool completely, then break apart any large chunks.
Make the Cinnamon Cream Cheese Frosting:
In a mixing bowl, beat the softened cream cheese and butter together on medium speed for 2–3 minutes until creamy.
4 ounces cream cheese, ½ cup unsalted butter
Scrape down the sides. Add the powdered sugar gradually on low speed.
3 cups powdered sugar
Add vanilla, cinnamon, and salt. Increase speed to medium-high and beat for another 2–3 minutes until smooth and fluffy.
¼ teaspoon vanilla extract, 1 teaspoon ground cinnamon, Pinch of salt
Assembly
Once cookies are completely cooled, spoon 1–2 tablespoons of the triple berry jam onto the center of each cookie. Spread evenly, leaving a slight border.
Fill a piping bag (or ziplock with a snipped corner) with the cinnamon cream cheese frosting. Pipe a swirl or dollop on top of the jam.
Sprinkle generously with the cinnamon streusel.
Serve immediately or chill for 10–15 minutes for a firmer texture.