In a saucepan, combine the sugar, ¾ cup cream, and the vanilla. Cook over low heat, stirring constantly with a wooden spoon, until the sugar is dissolved. Raise the heat and scald the mixture.
Meanwhile, place the arrowroot starch in a medium bowl. Using a wire whisk, gradually whisk in the remaining ¼ cup cream until smooth. Add the egg yolks and whisk until well blended.
Slowly pour ⅓ cup of the hot cream mixture into the yolk mixture, whisking constantly. Gradually whisk in the rest of the hot milk. Return the milk-yolk mixture to the saucepan and heat over medium heat for 2-3 minutes until thickened, whisking constantly.
Remove the pan from the heat and whisk in the oil. Transfer to a bowl, cover with plastic wrap, pressing it directly onto the surface, and refrigerate until chilled.
To make the donuts
Preheat oven to 350F and oil a doughnut pan with a dab of coconut oil. Set aside
Place all dry ingredients in a medium sized bowl and whisk to combine.
In a separate large bowl, combine all wet ingredients.
Add wet to dry and stir to combine. Allow to sit for 2-3 minutes to thicken up.
Place the batter in a piping bag or large ziploc bag with the end cut off the end so there’s about a ½-inch opening.
Fill each donut cavity ¾ to the top. Be careful not to overfill or the doughnuts will overflow while cooking.
Place in the oven to bake for 14-17 minutes, or until toothpick inserted comes out clean and edges are just beginning to brown.
Remove from oven and allow to cool for 1-2 minutes before grabbing the pan with an oven mitt and tipping over onto a cooling rack. Allow to cool completely (about 60 minutes)
To make chocolate topping
Meanwhile, add chocolate chips and coconut milk to a double boiler and melt completely. Then, slice donuts in half, like you would a bun for a sandwich. Scoop pudding on the bottom half and set back on the cooling rack. Dip the other half of the donut in the melted chocolate and top on the pudding half. Serve!
Notes
Sugar: feel free to use coconut sugar!
Recipe by Healthful Pursuit at https://www.healthfulpursuit.com/2014/02/boston-cream-donuts-gluten-free-paleo/