Prepare Kathi's Chocolate Cake Mix as directed. Spread dough onto a well greased and floured cookie sheet and bake for about 25-30 minutes at 350° F until toothpick comes out clean. (Baking times may vary depending on oven type and altitude.)
Place on cooling rack. Let sit for about 50 minutes and cool to room temperature.
Prepare the instant vanilla pudding as directed and let it cool to room temperature.
Rinse the apples before peeling, halve them lengthwise, remove the core and slice. Reserving 6 intact slices, cut the remaining apple slices into small cubes.
Melt sugar and butter in a pan until the sugar starts turning brown. Now caramelize the cubed apples.
Press a whiskey glass onto cooled cake layer, cutting out 12 circles. Place 1 circle in each glass. Top with 2 tbsp of the warm caramelized apples and a layer of pudding. Repeat the layers (cake, fruit, pudding) once more.
Beat the heavy whipping cream until stiff peaks form and spread it equally over all 12 glasses.
Cut the remaining sheet cake in pieces, put it on top of the whipped cream and place the apple slices decoratively on top.