Preheat the oven to 350F
In your mixer bowl, beat the butter, sugar and 1 tsp vanilla extract together in a for 3 minutes.
Add in the flour and mix together until just combined.
Use a 1 Tbsp size cookie scoop to scoop the dough. Roll each scoop in to a ball and place on your cookie sheet about 2 inches apart.
Use your thumb or a small spoon to press down and make an indentation in the center of each ball.
Fill each indentation with jam.
Bake at 350F for 14-16 minutes until the edges are lightly browned.
Remove from the oven and let the cookies cool on the cookie sheets for 3 minutes, then transfer to a cooking rack.
For the glaze, whisk the powdered sugar and milk together in a small mixing bowl until smooth. Only add enough milk until it whisks together but is the right consistency for drizzling. Drizzle over the cookies before serving