In a large bowl, whisk together flour, cocoa powder, baking powder, baking soda, and salt.
In a separate bowl, combine 1 cup sugar, buttermilk, melted butter, and eggs and whisk until smooth.
Slowly pour the wet ingredients into the dry ingredients and stir until just combined, taking care not to over-mix.
Lightly flour a surface and roll dough out into ⅓ thickness. Sprinkle some flour over the dough, too.
Using a 2 ½ inch cookie or biscuit cutter, cut rounds into dough. Re-roll dough scraps to get as many rounds as possible (should have about 30)
Put a caramel or 4 caramel bits in the center of a dough round. Pinch dough closed around the caramel and roll into a smooth ball. Continue with all of the dough rounds.
Cover a baking sheet with paper towels and fill a wide, shallow bowl with remaining ⅓ C sugar.
Heat canola oil in a large pot to 350 degrees. Once oil comes to temperature, place 5 dough balls in it. Let fry for 4 minutes total, turning halfway through. Remove doughnuts from oil with slotted spoon and place on paper towel-lined baking sheet.
Let doughnuts sit for 5 minutes before rolling in bowl of sugar. These doughnut holes can be eaten warm or at room temperature.