Prepare baking sheets by lining with parchment paper or silicone mats.
In a large bowl, add softened butter and powdered sugar. Using a hand or stand mixer, beat the butter together with the sugar on a high speed until it’s light and soft, approximately 2-3 minutes.
Once light and fluffy, scrape the sides of your bowl then add your vanilla extract and salt. Switch to a medium speed, then gently add the flour to the dough until it is just combined. The dough should be fairly sticky but still firm.
Form the dough into a ball, cover, and let it chill in the fridge for 30-60 minutes.
When ready to bake, preheat oven to 325° and position your rack in the middle of the oven.
After chilling dough, scoop out a few tablespoons of dough and roll them into about 1 inch balls. Place the dough balls onto the lined baking tray, spaced out evenly.
Using the handle end of a wooden spatula, or your finger, make a well in the center of each cookie dough ball. Make sure it’s deep, but don’t poke a hole all the way through. You also don’t want the well to be too wide.
To each cookie well, add a generous amount of raspberry preserves. You can use a small spoon to do this or a piping bag if it’s easier.
Bake the jam-filled cookies for about 20-25 minutes or until they’re golden brown, and they’ve puffed up. Let the cookies cool on the baking tray for 5 minutes before transferring them to a cooling rack to cool completely. Once they’re completely cooled, you can add an extra dusting of powdered sugar to the cookies if you’d like. Serve, and enjoy!