Prepare the cheesecake filling
Line a small baking sheet with parchment paper. Beat cream cheese, sugar, and vanilla until fluffy and smooth, about 2 minutes.
Portion the filling
Scoop the mixture into 20 portions (about 2 teaspoons each). Flatten slightly into discs and freeze until solid.
Make the strawberry jam
Add diced strawberries and sugar to a saucepan over medium heat. Cook for about 45 minutes, stirring frequently and gently smashing the berries.
Continue cooking until the mixture thickens and reduces to about 1/3 cup. Chill the jam in the refrigerator.
Prepare the cookie dough
Preheat the oven to 350°F (175°C) and line two baking sheets with parchment paper.
In a bowl, whisk flour, baking powder, baking soda, and salt.
In another bowl, cream butter and sugar until light and fluffy, about 2 minutes.
Add egg and vanilla and mix until pale and fluffy.
Add dry ingredients and mix just until combined.
Fold in the strawberry jam
Layer portions of dough with jam and gently fold to create small jam pockets without fully mixing.
Assemble the cookies
Scoop dough into 20 portions (about 2 tablespoons each). Flatten slightly, place a frozen cheesecake disc in the center, and seal the dough around it.
Shape each cookie into a slightly flattened disc and roll in sugar.
Place 6 cookies per baking sheet and bake for 11–12 minutes.
Let cookies cool on the baking sheet for 10 minutes before transferring to a rack.
These Strawberry Cheesecake Cookies will have soft centers with creamy cheesecake and sweet strawberry pockets.