Prepare a 9-inch springform pan by lining the sides with parchment paper that sticks about an inch above the sides of the pan.
To make the mousse, beat cream cheese and sugar for together in a large mixer bowl until smooth.
Add 2 tablespoons of milk to the cream cheese mixture and beat until smooth. Set the cream cheese mixture aside and make the whipped cream.
Whip heavy whipping cream and powdered sugar on high until stiff peaks form.
Carefully fold whipped cream into cream cheese mixture.
Divide the mousse between two bowls. You’ll want about 2/3 of the mixture in one bowl and the rest in another.
Gently fold the almond extract into the larger amount of mousse. Set aside.
Gently fold the raspberry jam into the smaller amount of mousse. Fold the raspberries into the raspberry mixture. Set aside.
Place the remaining 1/2 cup of milk in a small bowl. Place a single layer of shortbread cookies into the bottom of the pan, dipping each into the milk before adding.
Top the cookies with about 1/2 of the almond mixture and spread into an even layer.
Place another layer of shortbread cookies on top of the almond mixture, dipping them in the milk first.
Top the cookies with the raspberry mixture and spread into an even layer.
Place another layer of shortbread cookies on top of the raspberry mixture, dipping them in the milk first.
Spread the remaining almond mixture evenly on top of the cookies.
Refrigerate cake until firm, 4-5 hours or overnight.
Once firm, remove icebox cake from pan and set on a serving plate.
To make the whipped cream for on top, whip heavy whipping cream, powdered sugar and raspberry jam on high until stiff peaks form.
Pipe swirls of the raspberry whipped cream around the top edge of the cake and finish it off with fresh raspberries. Refrigerate until ready to serve.