These classic cookies have a nostalgic appearance and pack a mighty flavor punch. Piping the cookie dough is a fun change up from the normal scoop-and-bake cookie. Make sure to use room temperature butter for a dough that whips up nicely and is easy to pipe.
a small pastry bag; an 18-inch or larger pastry bag fitted with an open star tip (tip 1M)
Position racks in the upper and lower thirds of the oven and preheat to 325 degrees F. Line 2 baking sheets with parchment paper. Fit an 18-inch (or larger) pastry bag with an open star tip (such as Wilton 1M). If using disposable pastry bags, double bag them for more durability.
Place the raspberry preserves in a small pastry bag or small resealable plastic bag and set aside.
Combine the butter, sugar, vanilla, orange extract and salt in a stand mixer fitted with the paddle attachment on medium speed until light and smooth, 2 to 3 minutes. Scrape the bowl and paddle with a rubber spatula.
With the mixer running on low speed, add the egg then increase to medium speed and beat until smooth, about 1 minute. Scrape the bowl then add the flour and mix on low speed just until combined. Stir with a rubber spatula just until no streaks of flour remain. Transfer half of the dough to the 18-inch pastry bag.
Before piping the dough, use your finger to smear a tiny bit of the dough onto the corners of each baking sheet to help the parchment adhere. Pipe 5 round swirls of the dough, about 1 1/2 inches across, in 4 rows on one of the prepared baking sheets. Refill the pastry bag with the remaining dough and repeat the piping on the second prepared baking sheet. You should have about 40 cookies total.
Snip off a 1/4-inch opening on the bag with the raspberry preserves. Squeeze about 1/4 teaspoon of the preserves in the center of each cookie.
Bake, rotating and switching the positions of the baking sheets halfway through, until the cookies are golden, 24 to 25 minutes. Let cool completely on the baking sheets.
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