Add pure vanilla extract, cinnamon, and sweetened condensed milk to a large mixing bowl and blend completely.
Take half of your apple mixture and puree it.
Add pureed apples to condensed milk mixture and stir until evenly distributed.
In a separate mixing bowl add your heavy cream and mix until stiff peaks form.
Add half of your cream to your condensed milk mixture and fold until fully combined.
Add all but a couple tablespoons of your crushed cookies to your mixture and fold in until evenly distributed.
Add half of your ice cream to a freezer safe container and top with your other half of apple compote.
Add remaining ice cream on top, then the rest of your cookies and apple.
Seal your container and chill in freezer for at least five hours or overnight.