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If you’re using fresh strawberries, chop the strawberries into small bite-sized pieces if you haven’t already. Gently blot them with a towel to rid some moisture. (No need to thaw and blot if you’re using frozen strawberries.) The wetter the berries are, the more difficult they are to combine with the dough. Freeze the fresh chopped strawberries as you prepare the other dough ingredients. The colder, the better.
You can use a food processor for this step, but I encourage you to do it by hand so you don’t accidentally over-work the dough. Overworked dough lends tougher cookies. Whisk the flour, sugar, baking powder, and salt together in a large bowl (or pulse together in your food processor). Add the cubed butter and cut into the dry ingredients with a pastry cutter until coarse crumbs form. (Or pulse several times in a food processor.) See photo above for a visual. If you used a food processor in this step, pour the mixture into a large bowl.
Whisk the milk, egg, and vanilla extract together in a small bowl. Pour over the flour/butter mixture. Using a large spoon or rubber spatula, fold everything together until just about combined. The dough is thick, sticky, and tacky. Avoid overworking the dough.
Carefully work in the cold strawberries. Do not over-mix, which will turn the dough slimy. Some strawberries won’t combine into the dough at all and that’s ok. You can add them to the dough balls when you shape the cookies before baking.
Cover the cookie dough and chill in the refrigerator for at least 45 minutes and up to 1 day.
Preheat oven to 375°F (191°C). Line two large baking sheets with parchment paper or silicone baking mats. (Always recommended for cookies.) Set aside.
Using a Tablespoon measuring spoon or medium cookie scoop, portion/shape dough into balls about 1.5 Tablespoons of dough each. (If using a Tablespoon measure, it will be a heaping Tablespoon of dough.) Press any strawberries that haven’t stuck to the dough into the tops of the cookie dough balls. Arrange 3 inches apart on the prepared baking sheets. If desired for delicious crunch, sprinkle each dough ball with coarse sugar.
Bake the cookies for 15-16 minutes or until the edges are lightly browned.
Remove from the oven and let cool on baking sheet for 5 minutes. Transfer to a wire rack to cool completely before icing.
Using a fork, whisk confectioners’ sugar, 2 Tablespoons (30ml) of milk/heavy cream, and vanilla extract together in a small bowl. Add 1 more Tablespoon (15ml) of milk/cream to thin out if necessary. (I always add it, especially if using cream.) If desired for light strawberry flavor, whisk in strawberry jam. Drizzle over cookies.
Cookies stay fresh covered at room temperature for up to 1 day or in the refrigerator for up to 1 week.