Prepare pudding by following directions on package. Set aside.
Pour the whipping cream into a bowl and beat until stiff peaks form. Add to chocolate pudding and fold to combine.
Place the cookies into a resealable plastic bag and crush into chunks. Add to the pudding mixture and fold to combine.
Pour pudding mixture into each popsicle mold and place the popsicles in the freezer until frozen solid, about 4 hours or up to overnight.
Notes
If you do need a healthier alternative to whipping cream, we recommend using a vanilla Greek yogurt. You could also use a plain Greek yogurt, but the vanilla has a little bit better flavor.