Place the chopped strawberries, yogurt, milk and vanilla extract in a blender and pulse until smooth.
Stick some sliced strawberries into the inside of popsicle molds. Pour the popsicle mixture into the molds, insert popsicle sticks and freeze until solid, 3-4 hours.
Make the chocolate coating: Combine the chocolate chips and coconut oil and microwave at 30 second intervals until fully melted.
Unmold the popsicles by running the molds under hot water for 5-10 seconds. Dip the popsicles into the chocolate coating and turn upright to create a drip pattern. Serve immediately.