Prepare your workspace: Preheat your oven to 350°F. Line two large baking sheets with parchment paper or lightly grease them with baking spray.

Make the raspberry topping: In a medium saucepan, mix the raspberry jam, water, and vanilla extract. Bring it to a light boil over medium-high heat, then simmer for 3 to 5 minutes until the mixture becomes fully liquid and slightly thickened. Stir frequently, then remove from heat and allow it to cool to room temperature.

Create the cookie dough: In a large bowl, whisk together the sugar cookie mix and 1 cup of graham cracker crumbs. Add the softened butter, egg, and milk. Beat with a mixer until a firm dough forms.

Shape the cookies: With a 1 1/2 tablespoon cookie scoop, portion out the dough and roll each piece into a ball.

Flatten and bake: Coat each dough ball in the remaining 1/2 cup of graham cracker crumbs and place them on the prepared baking sheets, spaced 1 to 2 inches apart. Press each ball gently with the bottom of a glass until about 1/2 inch thick. Bake for 10 to 12 minutes until the tops are golden and cracked. Cool on the sheet for 5 minutes before transferring to a wire rack to cool completely.

Make the frosting: In a large bowl, beat the powdered sugar, softened cream cheese, vanilla extract, and salt until smooth and creamy. Gradually pour in the milk while mixing until the frosting becomes thick but pipeable.

Decorate the cookies: Once completely cooled, frost the cookies using a piping bag fitted with a round tip or simply spread the frosting with a knife or spoon. Top each frosted cookie with a teaspoon of the cooled raspberry topping or drizzle it over if preferred.