In a large bowl, mash together the strawberries and sugar until somewhat chunky and a lot of the natural juices have come out. Set aside.

Beat the heavy cream, vanilla and sweetened condensed milk on high until stiff peaks form, about 5 to 8 minutes. Be sure to not over beat the cream or else it'll turn to butter.

Pour the mashed strawberries, juice included, into the cream and fold until evenly distributed. It doesn't have to be completely mixed together. Some streaks of strawberry throughout is fine.

Divide the mixture into popsicle molds, insert wooden sticks and freeze until completely firm, about 6 hours or overnight.

To make the topping, place the cookies in a food processor and pulse until finely chopped. Pour out half of the crumbs into a shallow dish. Add the dried strawberries into the food processor with the remaining crumbs and pulse until the mixture comes together. Pour in the butter and pulse once more until coarse crumbs form. Add the strawberry cookie crumbs to the shallow dish and mix together.

Remove the popsicles from the molds and place on a baking sheet lined with parchment paper. Allow to sit for about 2 to 3 minutes to warm up the outside of the popsicles, this will allow the coating to stick. If you want to speed it along, you can place the palm of your hand on the popsicles to warm them up slightly. Coat each popsicle evenly and generously with the crumb mixture, pressing the crumbs onto the popsicles as much as possible. Return to the baking sheet and continue coating the rest.

Return the popsicles to the freezer for at least 30 minutes before serving. They can be kept in the freezer for up to 2 weeks. Enjoy!