In a medium saucepan, combine finely diced fresh strawberries with 1/4 cup of granulated sugar over medium heat. Stir gently while cooking for about 45 minutes, mashing halfway through, until it thickens.

In a mixing bowl, combine 8 oz of softened cream cheese with 1/4 cup granulated sugar and 1/2 tsp vanilla extract. Blend until smooth and creamy for about 2 minutes. Divide into 18 equal portions and flatten each one.

In a large mixing bowl, cream together 1 cup softened unsalted butter and 1 cup granulated sugar until light and fluffy—about 3-4 minutes. Add in one room temperature large egg and 1 tsp vanilla extract, mixing until well combined.

In a separate bowl, whisk together 3 cups of all-purpose flour, 1/2 tsp baking powder, and 1/4 tsp salt. Gradually add to the creamed butter and sugar, blending on low speed until just combined.

Divide cookie dough into four equal parts. Flatten a portion of dough and layer 1 tsp of homemade strawberry jam in the center. Fold the edges over to create pockets.

Preheat your oven to 350°F (175°C) while preparing the baking sheets with parchment paper. Place cookies about 2 inches apart and bake for 11-12 minutes until edges are lightly golden. Allow cooling for 10 minutes.