Preheat the oven to 375°F (190°C). Line two baking sheets with parchment paper.
In a medium bowl, toss the fresh raspberries with 0.25 cup granulated sugar. Set aside to macerate while preparing the dough.
In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla extract.
In a separate bowl, whisk together the flour, baking powder, salt, and cinnamon. Gradually add the dry ingredients to the wet mixture, mixing just until combined.
Gently fold in the macerated raspberries along with any accumulated juices into the cookie dough.
Scoop tablespoon-sized portions of dough onto the prepared baking sheets, spacing them about 2 inches apart.
In a small bowl, combine the oats, flour, cold butter, and a pinch of salt. Use your fingers to work the mixture into coarse crumbs. Sprinkle a generous amount over each cookie.
Bake for 12–15 minutes, or until the edges are lightly golden and the centers are set. Cool on the baking sheet for 5 minutes before transferring to a wire rack.
Notes
For best results, use fresh raspberries and avoid overmixing the dough to keep the cookies tender.