Preheat oven to 350F.

In a stand mixer bowl fitted with a paddle attachment, combine softened butter and sugar. Mix until light in color. Add the sifted flour in two to three additions while scraping in between each addition.

Transfer the dough to a lightly floured surface and roll the dough out to 1/4" thick and cut out with a 3" round cookie cutters.

Transfer the circles to a sheetpan lined with parchment or a silpat and refrigerate for 15 minutes. Bake the shortbread for 15-20 minutes or until golden brown. Let the shortbread cool on a cooling rack before decorating.

Combine your sifted powdered sugar and milk together. Whisk until smooth. Glaze half of the cookies with the icing. I left about a 1/4" border on the cookie.

Cut the glace cherries in half and place one in the center of the iced cookie immediately before it dries. Top the other cookies with jam and sandwich it with the iced cookie on top.