In a medium bowl, whisk together pudding mix and milk until completely incorporated.
Remove stems from strawberries, and cut them in half vertically.
Place one strawberry half in the bottom of a popsicle mold, cut side out. Fill mold with enough pudding to cover the strawberry. Place another strawberry into the mold, cut side out, and top with pudding. Repeat until mold is filled. Place popsicle stick into mold. Repeat with remaining popsicle molds.
Place popsicle mold in freezer for 5 hours. Run molds under hot water for a minute to loosen the popsicles. Remove popsicles from mold and enjoy!