Preheat & Prep
Preheat your oven to 350°F (177°C). Line large rimmed baking sheets with parchment paper.

Melt Butter & Combine with Peanut Butter
In a large microwave-safe bowl, microwave the butter in 20-second bursts until fully melted. Add the well-stirred natural peanut butter and mix until smooth.

Add Sugars
Stir in the brown sugar and granulated sugar into the warm butter-peanut butter mixture. Set aside to cool slightly.

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

Add Wet Ingredients
To the cooled peanut butter mixture, add the eggs, milk, and vanilla extract. Whisk thoroughly until the mixture is fully combined.

Combine Wet & Dry
Add the dry flour mixture into the wet mixture. Stir with a sturdy spatula or wooden spoon until the dough is fully formed and no dry flour remains.

Shape & Fill Cookies
Using a large spring-loaded cookie scoop (about 3 tablespoons), scoop the dough and roll it between your palms to create smooth balls.
Using your thumb, gently press a well into the center of each dough ball.

Add Jam Filling
Spoon in 1 heaping teaspoon of chilled strawberry jam into each well. Partially close the jam pocket by folding some of the surrounding dough over the top, but leave some jam peeking through.

Reshape & Place
Lightly roll the dough balls again between your palms for a round shape. Place on the prepared baking sheets with the jam side up. Leave about 3 inches between each cookie.

Bake
Bake the cookies for approximately 14 minutes, or until the edges are lightly golden and the cookies appear puffed up. Do not overbake.

Cool
Let the cookies cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.