Preheat your oven to 375 degrees and line a baking sheet with parchment paper or a silicone baking mat; then, without unrolling the crescent roll dough, cut it into 24 rounds (about a quarter-inch wide) and place them on your prepared baking sheet.
Lightly press the center of each dough round using your fingertips to create a slight well for the filling, then in a small mixing bowl, combine the softened cream cheese, 3 tablespoons of powdered sugar, and vanilla extract, mixing until smooth.
Spread about 1 teaspoon of the cream cheese mixture on top of each dough round, and then gently add about 1 teaspoon of the raspberry jam on top of the cream cheese filling.
Sprinkle each cookie with some of the sliced almonds and bake for 10–14 minutes, or until the edges are lightly golden brown, then remove from the oven and allow to cool on the pan for 5 minutes before moving to a wire rack to cool slightly more.
In a small bowl, combine the ½ cup of powdered sugar with enough of the milk for a thin drizzling consistency, then drizzle the glaze over the cookies and allow the glaze to harden before serving.