Combine coconut milk, vanilla, strawberry extract if using, and strawberries in a blender and blend until smooth. Pour into popsicle molds, insert sticks, and freeze for at least 6 hours.
Place cookies and freeze-dried strawberries in a small food processor and pulse several times until the mixture is crumbly with some texture.
Line a plate or sheet pan with parchment paper.
Pour melted chocolate into a glass. Remove ice cream pops from their molds and dip them into the chocolate to coat. Coat with the cookie mixture, place on prepared plate and place back in the freezer for 30 minutes.