Line a small cookie sheet with parchment paper. In a small bowl, combine the cold cream cheese, sugar, and vanilla extract. Using an electric mixer on medium-high speed, beat until the mixture is light, fluffy, and the sugar has dissolved, about 2 minutes. Scoop out 18 portions of 2 teaspoons each onto the baking sheet, flattening slightly to form thick discs. Freeze until completely solid.

In a medium pot over medium heat, combine the diced strawberries and sugar. Cook, stirring occasionally and smashing the berries with a wooden spoon halfway through, for about 45 minutes until thickened and reduced to about 1/3 cup (80 ml). Stir more frequently near the end to prevent burning. Remove from heat and chill in the fridge.

Preheat the oven to 350℉ (175℃). 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, use an electric hand mixer or stand mixer fitted with a paddle attachment to beat the softened butter and granulated sugar on high speed until light and fluffy, about 2 minutes.

Beat in the egg and vanilla extract on medium speed until the mixture is pale and very fluffy, about 1–2 minutes.

Add the dry ingredients to the wet mixture. Mix on low speed until just combined; be careful not to overmix to keep the dough tender.

Push three-quarters of the dough to one side of the bowl. Flatten one-quarter of the dough on the bottom and spoon one-quarter of the chilled strawberry jam over it. Repeat layering the remaining dough and jam so the jam is dispersed throughout the dough. Use a spatula to divide the dough into quarters and gently fold each until the jam is swirled in, not fully mixed.

Using a 2-tablespoon cookie scoop, scoop dough into 18 portions. Flatten each portion slightly, place a frozen cheesecake disc in the center, and wrap the dough around the filling to seal completely. Shape each into a slightly flattened disc.

Roll each dough disc in the additional 1/4 cup granulated sugar to create a sweet, crisp exterior.

Arrange 6 cookies per prepared baking sheet, spaced apart. Bake in the preheated oven for 11 to 12 minutes until cookies are set but not browned. Immediately after baking, use a circular cookie cutter to neaten the shape if desired. Let cookies cool on the baking sheets for 10 minutes, then transfer to wire racks to cool completely before serving.