Preheat the oven to 350 degrees Fahrenheit.
Spray your donut pan generously with cooking spray.
In a large mixing bowl, combine all the wet ingredients including butter, oil, eggs, vanilla extract, and milk. Stir in the sugar.
In a separate bowl, combine the flour, cocoa powder, baking powder, and espresso. Stir to combine.
Add the flour mixture to the wet ingredients mixing well to form a sticky dough.
Spoon the dough into a large piping bag or ziplock bag. Cut off one of the corners of the bag, twist the top closed, and pipe dough into the donut pan, filling each circle 3/4 of the way full.
Bake donuts for 10-12 minutes or until toothpick inserted into donut comes out clean and top of donut springs back with gently pressed with your finger.
Transfer to cooling rack.
To make the glaze, sift together the powdered sugar and cocoa powder. Use a whisk to sir in 2 tablespoons of the coffee and the vanilla. If glaze is still too stiff, add another 1 tablespoon of coffee. Add a second tablespoon if needed until glaze reaches a pourable consistency.
Dip the top of each cooled donut into the glaze. Transfer to cooling rack and sprinkle with crushed raspberries, gently pressing the raspberries into the glaze.
Allow glaze to stiffen before serving. Best served the day they are made.