These were some of my favorite cookies growing up — there were a bunch of amazing Italian bakeries outside of Chicago and I was always drawn to these cookies because of the sprinkles. But what really gets me is that soft layer of jam in the middle that makes the cookies a little bit chewy (and that splash of almond is irresistible as well).
18-inch piping bag and large open star piping tip (such as Ateco #829)
Place oven racks in the top and bottom third positions. Preheat the oven to 350 degrees F.
Line 2 rimmed baking sheets with parchment paper and set aside.
Whisk together the flour, salt and baking powder in a medium mixing bowl. Add the butter and sugar in the bowl of a stand mixer fitted with the paddle attachment and beat on medium-high speed until light and fluffy, 1 to 2 minutes. Add the egg, vanilla and almond extracts and beat until light and smooth, 1 minute more. Reduce the speed to low and add the flour mixture. Beat until just combined.
Transfer the dough to a piping bag fitted with a large open star tip. Pipe the dough onto the prepared baking sheets in 2-inch lines, spaced 1-inch apart (you should be able to fit 12 cookies per tray). Bake in the oven until the cookies are set on top and golden around the edges, 12 to 15 minutes. Cool completely on the sheet trays. Once the cookies are set, transfer all onto one tray, leaving 1 cooled tray to bake the remaining dough (you’ll have enough for about 12 more cookies).
Melt the chocolate and coconut oil in a double boiler or in the microwave on 50-percent power in 15 second increments. Pipe or spread the flat sides of half of the cookies with about 1 teaspoon jam each, going almost to the edges. Sandwich with the remaining cookies (you should have about 18 sandwiches). Allow the jam to set for 2 hours or overnight, if you have time. Otherwise, it’s okay to go ahead and start dipping your sandwich cookies into the chocolate (it just might be a little slippery.).
Dip the lower third of the cookies in the chocolate letting the excess drip back into the bowl. Sprinkle with the sprinkles on both sides. Lay back on a parchment lined baking sheet and pop the cookies in the refrigerator for about 10 minutes to let the chocolate set.
Tip: To make uniformly sized cookies, use a ruler and a marker or pen to draw 2-inch lines on 2 sheets of parchment paper in a 3-by-4-inch grid. Flip the parchment over and place on 2 baking sheets so the marker side is down but you can still see the lines. Using the lines as a template, pipe the dough in 2-inch lines on the baking sheets, using a paring knife or shears, if needed, to cut the dough from the piping bag in straight edges.
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Tools You May Need
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