In a medium saucepan, combine diced strawberries and 1/4 cup granulated sugar. Cook over medium heat for about 45 minutes, mashing halfway through, until thickened and reduced to about 1/3 cup.

In a bowl, mix cream cheese, 1/4 cup sugar, and 1/2 tsp vanilla extract until smooth. Divide the mixture into 18 equal portions and flatten each into a disc. Freeze until completely solid.

In another bowl, beat the softened butter and 1 cup sugar together until light and fluffy.

Add the egg and 1 tsp vanilla extract, continuing to beat until the mixture is pale and voluminous.

In a separate bowl, whisk the flour, baking powder, and salt. Gradually add this to the butter mixture until just combined.

Divide the dough into four parts in the mixing bowl. Layer jam between flattened sections of dough to evenly distribute.

Cut the dough into quarters and gently fold each section to create pockets of jam without fully blending.

Scoop dough into 18 two-tablespoon portions. Flatten each piece, place a frozen cheesecake disc on top, and wrap the dough around to fully encase the filling.

Shape into slightly flattened discs and arrange cookies on baking sheets.

Preheat your oven to 350°F (175°C) and bake for 11-12 minutes.

Allow to cool on the tray for 10 minutes before transferring to a wire rack to cool completely.