Combine the flour and granulated sugar in a large mixing bowl then sprinkle in the diced butter. With a pastry blender, moving in an up and down and twisting motion cut the mixture multiple times until the mixture is uniform and resembles coarse crumbs.

In a small bowl whisk the egg, vanilla and milk and add it to flour/butter mixture. With a spatula, stir to combine, until a thick ragged dough starts to form. Add 1 tablespoon more milk if necessary.

With floured hands, knead the dough in the bowl until it becomes one uniform clump of dough. Divide the dough into two equal portions, form 2 balls and flatten into 4” – 5” disks. Wrap each disk tightly in plastic wrap and refrigerate for at least 2 hours or overnight.

Bring refrigerated dough to room temperature for 10 – 15 minutes. Meanwhile, preheat oven to 350 degrees F. Prepare 3 large baking sheets by lining with parchment paper.

Lightly flour a clean work surface. Roll out one disk at a time to about ⅛” – ⅙” thickness. While rolling sprinkle the top of dough lightly with more flour as needed.

Cut desired shapes with cookie cutters. For half of the shapes, cut out a small circle hole in the centre (an apple corer is just the right size for the hole). Re-roll the scraps, repeating the process to make more cookies until all the dough is used. If desired, with some of the re-rolled scraps, cut out mini shapes to use as an accent when displaying the cookies (these mini shapes won’t be filled).

Transfer the cookies to the prepared baking sheets. If making mini cookies, place them on a separate baking sheet as they will bake a little quicker.

Bake for 8 - 10 minutes (less for mini cookies) to a light golden colour; do not over-brown. Remove from oven and let cookies set on baking sheet for 2 minutes before removing to a rack to cool completely.

To assemble the cookies, spread the “underside” (bottom baked side) of the solid cookies with about ½ teaspoon of jam, spreading almost to the edges. Cover with the cookies with a hole (placing the hole cookies baked side down), taking care to match the cut-out pattern. Press down very lightly.

Transfer filled cookies in one layer to a parchment lined surface. With a sifter or a small sieve, lightly dust the tops with icing sugar. Store cookies in an air-tight container, with sheets of parchment paper between layers, for 12 – 24 hours before serving.