In a large bowl, beat together oil, butter, and sugars until fluffy. Add eggs one at a time, beating well after each egg. Beat in vanilla.
In a separate bowl, combine flour, cocoa powder, baking soda, baking powder, and salt. Stir with a whisk. Gradually add flour mixture to the butter mixture, alternating with the milk, beginning and ending with the flour mixture. Beat until well blended.
Place 2 T of batter into each Silicone Cupcake Liner (with or without tray) and bake for 12-17 minutes. When done, toothpick inserted into center will come out with only a few dry crumbs.
Remove cupcakes immediately from Liners. Transfer to wire rack to cool.
Using the point of a pairing knife or other small knife, cut a small well in the top-center of each cupcake. Reserve each cut-out top. Fill each well with cherry preserves. Replace reserved tops onto each cupcake. Top each with frosting. Garnish with fresh cherries dipped in chocolate, if desired.
For Frosting
Beat butter on medium speed until fluffy. Gradually beat in powdered sugar until light and fluffy.
Beat in the cream until frosting reaches spreadable consistency. Add cherry preserves. If frosting becomes too loose or looks curdled, add more powdered sugar 1 T at a time until frosting comes together once again.