To make the thumbprint cookies:

• In the bowl of a stand mixer fitted with the paddle attachment, cream the butter and sugar together on medium speed until very light and fluffy, 4 to 5 minutes, scraping down the sides of the bowl halfway through and again at the end. Add the egg yolks, vanilla and almond extracts, and kosher salt and mix on medium speed until fully combined, about 30 seconds more.
• Sift the cake flour directly into the mixing bowl. Mix on low speed until the dough comes together, being careful not to overmix. If there’s excess flour on the sides of the bowl, use a rubber spatula to scrape down and do a few gentle turns to incorporate into the dough.
• Wrap the dough tightly in plastic wrap and place in the fridge to chill for at least 3 hours, up to overnight.
• Preheat the oven to 350°F and line 2 baking sheets with parchment paper. Place the turbinado sugar in a small bowl and set aside. In another small bowl, stir together the raspberry jam and orange zest and set aside.
• Pinch off pieces of dough and roll between the palms of your hands to form 1-inch balls. Roll each dough ball in the turbinado sugar, then place on the prepared baking sheets, spacing about 2 inches apart (NOTE: if you’re baking in batches, keep dough that you’re not working with in the fridge until ready to use). Using the back of a 1/4 teaspoon or the end of a wood spoon, create a well in the center of each ball. If the dough cracks, simply pinch it back together with your fingers. Fill each well with raspberry jam, then place in the fridge to chill for 15 minutes (this helps the cookies keep their shape in the oven).
• Bake for 12 to 14 minutes, until the edges of the cookies are set. Allow the cookies to cool for 10 minutes on the baking sheet before removing to a wire rack to cool completely.

To make the almond glaze:

• Place the powdered sugar, vanilla extract, almond extract, and milk in a small bowl, and whisk to combine. If necessary, add more milk, 1 teaspoon at a time, until you’ve reached the desired consistency for drizzling. Drizzle over the cooled cookies and allow to set, about 30 minutes.