Combine the butter and sugar in a large bowl. Add the eggs, one at a time.
In a separate bowl, sift together the flour, baking powder and salt. Stir the milk and vanilla together.
Add the flour mixture and the milk alternately to the butter mixture until just combined.
Stir in the cranberries and chocolate chips.
Preheat the cake pop maker and fill each cooking cavity with batter (fill it to just below the top of each cavity to avoid overfilling it). You can use a spoon or piping bag.
Close the lid and bake for 3 to 4 minutes or until a toothpick inserted into a cake ball comes out clean. Allow the cake balls to cool completely prior to coating.
Microwave the chocolate chips and coconut oil in a small bowl for 30 seconds and then give it a stir. Place the bowl back in the microwave and repeat cooking for 15 second intervals/stirring until fully melted. Be careful because if you overcook it the chocolate will get lumpy and hard.
Dip the tip of a lollipop stick in the melted chocolate and insert about halfway into a cake ball. Place it upside down on a plate or cake pop stand. Repeat with all cake balls and then refrigerate for 30 minutes.
Dip each cake pop into the melted chocolate (you may have to melt it again) and gently tap off the excess. Place it in a stand and repeat with the remaining cake pops.
Sprinkle with the cinnamon and chopped, dried cranberries. Let the chocolate set in the fridge for about 30 minutes and serve!
Notes
Make sure the cake pop maker is fully preheated before adding the batter or the cake balls won't bake properly. There should be an indicator light that says something like 'ready' to show when it's hot enough.
If some of the batter leaked around the cake balls, just wait for them to cool so that it crisps up, then break the excess off.
A small spatula helps to remove the cake balls from the cake pop maker.
Room temperature storage: Store the cake pops, covered, in a cool and dry place for up to 1 week.
Refrigerator storage: If you want to store them in the fridge, line a container with paper towel and place them in there with another piece of paper towel on top, to help absorb any excess moisture. You can store them this way for about 2 weeks.
Freezer storage: You can also freeze them for up to 3 months.