In a small bowl, beat cream cheese, powdered sugar, and vanilla until smooth and creamy.
Scoop teaspoonfuls onto a parchment-lined plate, freeze for at least 15–20 minutes. This step makes stuffing cookies much easier and keeps the filling gooey.
Cream butter, brown sugar, and granulated sugar until light and fluffy.
Beat in eggs and vanilla until combined.
In a separate bowl, whisk flour, baking soda, and salt. Gradually add dry mixture to wet; mix just until combined.
Fold in graham cracker crumbs for extra cheesecake flavor (optional).
Preheat oven to 350°F (175°C) and line baking sheets with parchment.
Scoop a tablespoon of cookie dough, flatten into a disk. Add a frozen cheesecake dollop and a drizzle of caramel sauce.
Top with another tablespoon of dough, sealing edges. Roll gently into a ball, ensuring cheesecake/caramel is enclosed.
Repeat and arrange cookies 2 inches apart on your baking sheet.