Combine garlic, butter, and spices in an oven proof bowl
Bake in 350F oven for 20 minutes
Add the tomato paste, stir well and bake for an additional 10 minutes. Remove from heat. Set aside.
Potatoes & Cheeses
Prepare skin on and skin off potatoes separately by boiling each for 20 minutes in salted water that covers the potatoes. Set each aside.
In a blender or food processor, combine the skin on potatoes with the half and half, 1/4 cup chopped pepperjack cheese, and wine. Add the prepared Sun Dried Tomato Garlic Herb Butter. Blend well until very smooth and creamy.
In a stand mixer, stir the skin off potatoes. Slowly add the blended potato and butter mixture.
Once well blended, add the remaining 1/4 cup finely chopped pepperjack cheese. Set aside.
To make one cheese cup each: In microwave, heat 1/2 cup shredded cheese about 20-30 seconds. Stir well, and pour on top of an upside down 6 oz oven proof broil safe bowl. Gently mold around the bowl just so cheese reaches over the top edges of the upside down bowl. Under a broiler, broil for 40 to 60 seconds, rotating every 20 seconds, until cheese is nicely browned. Remove from heat, and if necessary, carefully use a spoon or fork to fix any holes in the cheese bowl. Let it set until cooler, but still easily removable from the bowl. Remove from bowl and flip right side up and place inside the bowl, right side up. Reduce oven heat to 350F and bake cups for 5 minutes. Allow to cool, cheese cups should hold shape. If not, return to oven for a couple more minutes until a little more crisp so that when it cools, it holds shape.
To make cheese chips: Take sliced pepperjack squares and cut into triangles (in half diagonally). Set on baking sheet and bake in 350F oven for 6 minutes. Remove from heat. Let cool a couple minutes, then carefully flip chips over and bake an additional 1 or 2 minutes. Let cool completely.
To assemble: Scoop mashed potatoes inside a cheese cup and sprinkle with fresh chopped chives. Serve with cheese chips on the side and use to dip the mashed potatoes.