Preheat the oven to 325ºF (165ºC) and have a 24-cavity or two 12-cavity mini muffin tins ready, preferably non-stick.
Make the shortbread shells:
Place the butter in a mixing bowl and sift in the powdered sugar. Mix with an electric mixer at medium-high speed until pale and creamy, about 1 minute. Add the flour and salt, then mix on low speed until the mixture is crumbly with no bits of dry flour remaining. Use your hand to gently gather and knead the dough in the bowl until it comes together.
Divide the dough into 24 pieces (approximately 12 grams each) and roll each piece into a smooth ball between your hands. Place one ball in each mini-muffin cavity. Dip the rounded back of a 1-teaspoon measuring spoon in flour, then press it into the middle of a dough ball until you feel the back of the spoon touch the bottom of the pan and you can see the metal faintly through the dough. Repeat with the remaining 23 dough balls.
Bake the shells for 20 to 22 minutes, or until light gold around the edges. Set the pan on a rack to cool for 5 minutes, then transfer the shells directly to the rack to cool completely.
Make the date filling:
While the pastry shells are baking, chop the dates into tiny pieces. Add the dates, water, brown sugar, and salt to a small pot. Cook over medium-high heat for 6 to 7 minutes, gently boiling until the water is absorbed and the dates have broken down into a thick paste. Remove from the heat and set aside to cool.
Make the icing:
For the icing, place the butter, maple extract, and vanilla extract in a mixing bowl. Beat at medium-high speed until well combined, about 30 seconds. Sift in the icing sugar and mix well, then add the milk and mix until smooth. Transfer the icing to a piping bag fitted with your chosen tip.
Assemble the pork pies:
Spoon the date filling evenly into the 24 cooled shortbread shells. Pipe a small rosette of icing on top of each. Arrange the pork pies on a serving platter and keep them at room temperature until ready to serve.
Notes
Greasing the mini-muffin tin(s) is not usually necessary since the dough has enough butter, but if your pan isn't non-stick, a very light coating may help.
You should see the pan faintly through the pressed dough. If the cups are too thick on the bottom, they won't have enough room for the filling.
Don't worry if the shells turn deeper gold around the edges, they will still taste amazing. I use and recommend an oven thermometer for accuracy.
Storage
Store the pork pies in an airtight container at room temperature for up to 3 days or in the fridge for up to 1 week. Bring chilled tarts to room temperature before serving. They can also be frozen in an airtight container for up to 1 month.