In the bowl of a food processor, blitz the cookies into fine crumbs.
In the bowl of a stand mixer fitted with the whip attachment, beat the cream until medium-soft peaks form, 3 to 5 minutes.
Add the sweetened condensed milk and continue whipping until medium-stiff peaks form, 2 to 4 minutes more.
Spoon the cream into a resealable plastic bag and snip off one of the bottom corners of the bag to make for easy piping.
In individual glass serving dishes, wine glasses, martini glasses, short Mason jars, or a single large serving dish, alternate layering the cream and the cookie crumbs beginning and ending with the cream. You should have about 7 layers.
Garnish with anything you desire, whether ground cinnamon, almonds, toasted coconut, or the very untraditional (though stunning) passion fruit pulp and seeds.
Refrigerate at least 4 hours or preferably overnight to allow the cookies to soften. If chilling overnight, tent the puddings with plastic wrap to avoid it drying out.
Serve cold and garnish, if desired, with cinnamon, almonds, coconut, and/or passion fruit just before serving.