Choose your desired containers (e.g. glass cups, trifle bowls) that are enough to hold about 6-cup of pudding.
Crush the cookies in a food processor until very fine. If you do not have a food processor, put the cookies in a Ziploc bag. Close the bag tightly. With a rolling-pin, crush and roll the cookies until very fine.
In a large mixing bowl with an electric mixer fitted with a whisk attachment, beat the cream until soft peak forms. Add vanilla and just ½ of the sweetened condensed milk. Whip everything together and taste to try. If it is not sweet enough, add more sweetened condensed milk. Beat until stiff peak forms.
Place a layer of whipped cream at the bottom of a container. Smooth out the cream with a spoon, especially around the edge. Sprinkle a layer of cookie crumbs over evenly. Gentlely press down the crumbs with a clean spoon. Repeat with another layer of whipped cream, and then another layer of crumbs. Continue with the layers to a desired level. Finish with crumbs over the top of the pudding. Repeat with other containers.
Cover the containers with plastic wrap. Chill in the freezer for at least 6 hours (best overnight). Leave the pudding at room temperature for 15 - 20 minutes to soften before serving.