Line baking sheet with parchment paper and set aside.
In a large bowl, mix butter, sugar, vanilla extract, and flour together until incorporated. Dough should hold its shape when squeezed together.
Divide dough into 4 equal portions and form into logs down the length of the cookie sheet.
Press your finger into the center to create an indent all down each log.
Bake 12-15 minutes. Cool completely.
Fill each log with jam.
for the icing-
In a small bowl, mix together powdered sugar, 1 teaspoon of milk, and vanilla extract until its the consistency of white school glue. Add more milk as needed for desired consistency.
Drizzle icing over each log generously. Allow to set for 20-30 minutes before slicing.
Using a sharp knife, slice diagonally into 60 equal sized cookies and serve!
Video
Notes
Storage Directions
Allow cookies to cool completely to room temperature before storing. For best results, place parchment paper in between layers of cookies in an airtight container. This will prevent the cookies from sticking to each other and from drying out.Shortbread cookies should be eaten within a week or two. If you used jam as your filling, you might want to store your cookies in the fridge. This may soften the shortbread texture slightly.