Preheat oven to 400 F.
Cream the butter with an electric stand mixer or hand mixer. Add the sugar a little bit at a time as you continue to run the mixer, beating until creamed, fluffy, and light.
Add the egg yolks one at a time, followed by the vanilla and salt. Mix well to combine.
Add the flour 1/3 at a time, mixing well in between until a stiff dough forms.
Assemble and fill the cookie press. Press floral design cookies onto an ungreased cookie sheet about 2 inches apart. Using a chopstick or something similar, create a small hole in the center of each cookie. Fill the hole with about 1/8 tsp raspberry jam.
Bake cookies for 8-10 minutes until very lightly golden brown. They overbake and turn brown quickly, so keep a close eye at the 7 minute mark!
Remove cookies from oven and let cool completely on a wire rack.