Add the brown sugar to a medium sized mixing bowl. Zest the orange into the sugar, then use your fingers to rub the zest into the sugar.
Add in the butter. With a hand mixer or a stand mixer fitted with the paddle attachment, beat together the butter and brown sugar until the mixture is light and fluffy (2-3 min.)
Beat in the egg and vanilla until well combined.
Add in the flour, baking powder, and salt. Beat the ingredients together just until no flour streaks remain.
Cover the dough and leave it in the fridge to chill for at least 30 minutes, or for up to 2 days.*
Macerated Strawberries
Wash and dice up the fresh strawberries.
Transfer the diced strawberries into a small mixing bowl. Add in the fresh orange juice and sugar, and mix until well combined. Cover the bowl and place it in the fridge until you're ready to assemble the cookies.
Once you're ready to bake the cookies. preheat the oven to 350°F / 175°C. Line a cookie sheet with parchment paper or with a silicone baking mat.
Use a 3 tbsp. cookie scoop to dish out the cookies onto the prepared cookie sheet. Evenly space the cookies apart to allow room for spreading. Bake for 10-12 minutes, until the sides of the cookies start to turn golden brown.
Immediately after taking the cookies out of the oven, take a bowl that is slightly larger than the cookies and swirl it around over the cookies to make them a little more uniform and circular.
Vanilla Cream
Add the heavy cream, instant pudding, and sugar to a medium sized mixing bowl. Beat the mixture with a hand mixer (or with a stand mixer fitted with the whisk attachment) for 2 minutes, or until the cream thickens. Place the cream in the fridge until you're ready to assemble the cookies.
Once the cookies have cooled to room temperature, place a heaping scoop of the vanilla cream on top of each of them. Use a spoon to make a divot in the center of the cream for the strawberries, then top each cookie with the macerated strawberries. Serve and enjoy!
Notes
*If you're chilling them overnight, you'll want to take the dough out for at least 30 minutes before baking until the dough is warm enough to be scoopable again. Also, wait to macerate your strawberries until this point if you are not baking the cookies off the same day you make them.Store extra frosted cookies in an airtight container in the fridge.