Heat oven to 350 degrees Fahrenheit. Line cupcake pan with liners and spray with olive oil spray. Grease and flour pan(s) if making a cake.
Stir flour, cocoa powder, coconut sugar, baking soda, baking powder, and salt in a large bowl. If you have clumps of coconut sugar, you can use a fine mesh strainer to sift the ingredients together, so they are well blended. Then use the back of a spoon to push the clumps of sugar through the strainer to breakup the big clumps.
Add milk, eggs, olive oil, and vanilla extract and beat with a whisk or electric mixer until smooth, about 2 minutes. The batter will be very thick.
Microwave water in coffee mug for 90 seconds. Add hot water to the batter and mix well to combine. The batter will become very watery.
Pour batter into the pans or cupcake pan. Scrape any batter clinging to the bowl with a spatula.
For cupcakes: bake for 18 to 20 minutes until a toothpick poked through the middle of the cupcake comes out clean. Cool on a wire rack. Makes 24 cupcakes.
For 9” round pans: bake for 30 to 35 minutes until a toothpick poked through the middle comes out clean. Let the cakes cool in the pans on a wire rack for 20 minutes.
For 13” x 9” x 2” baking pan: bake for 35 to 40 minutes until a toothpick poked through the middle comes out clean.
While the cupcakes are cooling, put softened cream cheese and sugar into a mixer with a whisk attachment. You can also place it in a bowl and use a hand mixer. Mix on medium speed for about 3 minutes until slightly whipped. Add heavy whipping cream to bowl. Mix/whisk on medium-to-medium-high speed for about 5 minutes until it looks like it doubled in volume. Makes 4 cups of frosting.
Once the cupcakes are cool, frost with the cream cheese and whipped cream frosting. Use about 2 tablespoons of frosting per cupcake. You will have about ½ cup of frosting leftover.