Preheat the oven to 325 degrees F. Line muffin pans with paper liners.
In a mixing bowl, mix together the granulated sugar, gelatin, butter and cream cheese.
Beat in the eggs, one at a time, and stir in the vanilla and rum.
Combine and baking powder, add to the creamed mixture and mix very well.
Stir in the milk and strawberries until batter is smooth. Bake for around 25 minutes.
Allow to cool.
In a medium bowl, cream together butter and cream cheese.
Mix in the confectioners' sugar and strawberry extract.
Slice the strawberries into small pieces and place into a medium saucepan.
Add the sugar and bring to a light boil.
Once the filling begins to boil, turn off the heat and let sit for 10 minutes to cool.
Core out the center of the cupcakes and fill with strawberry filling.
Cover the tops of the cupcakes with the strawberry frosting.