Line a small cookie sheet with parchment paper. In a small bowl, combine the cold cream cheese, 3 tablespoons of granulated sugar, and vanilla. Blend until fluffy with an electric mixer on medium-high speed for about 2 minutes.

Scoop the mixture into 18 portions of about 2 teaspoons each and flatten them slightly to form thick discs. Freeze until completely frozen.

In a medium pot over medium heat, mix together the diced strawberries and the 1/4 cup of sugar. Cook for about 45 minutes, smashing strawberries halfway to create thick jam. Stir continuously until done, then chill in the refrigerator.

Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper.

In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.

In a large bowl, beat the softened butter and remaining cup of sugar using an electric mixer on high speed until fluffy (about 2 minutes). Add the egg and 2 teaspoons of vanilla, mixing on medium speed until pale and very fluffy (1-2 minutes).

Combine the dry ingredients with the wet mixture on low speed until barely incorporated.

Push 3/4 of the dough to one side of the bowl, flatten a quarter of the dough on the bottom, spoon a quarter of the strawberry jam onto it, and top with another quarter of dough. Repeat this two more times without fully mixing.

Using a 2-tablespoon cookie scoop, portion out 18 portions, flatten each portion, place a frozen cheesecake disc in the center, and encase it with dough. Roll in reserved granulated sugar.

Place the cookies on the prepared baking sheets (in batches of about six) and bake for 11-12 minutes. Use a large circular cookie cutter to shape cookies after baking.

Let cool for about 10 minutes on the baking sheet, then transfer to a cooling rack to cool completely.