In a large bowl, whisk together 2 1/2 cups flour, powdered sugar, and salt. Add cold cubed butter.

Use a pastry cutter, two forks, or your fingertips to rub the butter into the flour until the mixture resembles coarse crumbs with some pea-sized bits of butter left.

Mix in the egg yolk and vanilla. Stir until a soft dough forms. If it feels too dry, add 1 teaspoon cold water at a time until it comes together.

Shape the dough into a disk, wrap it, and chill for 20–30 minutes.

In a medium bowl, combine 3/4 cup flour, granulated sugar, cinnamon, and a pinch of salt.

Add softened butter and mix until it forms coarse crumbs.

Cover and chill if butter becomes too soft while shaping cookies.

Preheat oven to 350°F (175°C) and line baking sheets with parchment.

Roll the chilled dough into 1-inch balls and slightly flatten each ball on the baking sheet.

Make a small indentation in the center of each cookie using your thumb or the back of a small spoon.

Spoon about 1/2 teaspoon of raspberry jam into each indentation.

If using fresh or frozen raspberries, tuck one raspberry into the jam.

Sprinkle about 1 teaspoon of crumble topping over each cookie.

Bake for 12–15 minutes, until the edges are lightly golden and the crumble is set.

Rotate pans halfway if baking multiple sheets.

Let the cookies cool on the sheet for 5 minutes, then move to a wire rack to finish cooling.