Place shredded coconut in a nonstick pan over medium heat. Cook for 3-5 minutes, stirring frequently until evenly browned (not every strand of coconut needs to be browned perfectly).
Cut cold butter into cubes and place in a large bowl. Add brown sugar, vanilla and blend until creamy using a pastry blender or electric mixer.
Next add flour + salt and continue to blend in the same manner until the mixture begins to form a dough that you can press together with your hands. Add toasted coconut and cut in until fully combined.
Preheat oven to 325.
Place a piece of parchment paper down on your work surface. Spray surface lightly with non-stick spray as well as a rolling pin. Roll out to 1/8 inch thick. Place in fridge for 5 minutes. Test the firmness of the dough—try cutting out one pineapple. If you don’t get a nice clean cut, return to the fridge until the dough is firm.
Cut out as many pineapples as you can and place them on an ungreased cookie sheet. Bake for 20-25 minutes or until the edges are golden brown. Place on a wire rack to cool.
Repeat the process of rolling out dough, placing in the fridge, cutting out pineapples and baking until dough is gone.
Icing/Decorating
Whisk together marshmallow creme, powdered sugar, milk, pineapple extract and salt until fully combined and creamy. Separate 1/3 cup icing into a small bowl. This is for the green tops. Add drops of green until desired color is reached. I like to add a very small dot of black to get a different hue.
Prepare a piping bag with a no. 6 wilton tip and empty icing into the bag. Have either parchment paper or a wire rack to place finished pineapples on.
Pipe the pineapple tops on all cookies: trace an outline with the icing around the edge of the cookie top, then fill in. Use the nozzle or a toothpick to blend and smooth out the icing. Don't worry about any minor bumps or peaks that happen at this point, they will settle and smooth out on their own.
Continue with this process until all pineapple tops are iced. Mix the yellow icing and repeat the proces on the pineapple bottoms. Decorate with sprinkles.
Enjoy!
Notes
I used this piping tip size because my cookies were quite large (4 inches long). If you use a smaller cookie cutter, you might want to use a tip size 2.
These will still be delicious without the pineapple flavor if you aren’t into that. You could try pineapple juice as a replacement for all the liquid in the icing (milk and extract) but don’t think you will get a very strong pineapple flavor through all that sugar.
Making sure the dough is firm when you cut your shapes is key! Don’t skip refrigerating if you want the cookies to hold their shape.