First, make the pudding. Combine 2 cups of the milk and the sugar together in a medium sauce pan over medium heat. Let it come to a gentle simmer. While that happens whisk the egg yolks together in a bowl. Then in a separate bowl stir the other 1/4 cup of milk thoroughly with the corn starch. Scoop a 1/2 cup of the hot milk into the bowl with the egg yolks and whisk them together to temper the eggs. Then whisk that mixture back into the pot with the rest of the milk, letting it cook for just 15-20 seconds. Continue to whisk while you pour in the cornstarch mixture. Let the pudding bubble and thicken for a minute while you keep whisking, then finally whisk in the banana extract and butter until it is smooth. Transfer the pudding to a bowl and place plastic wrap directly on it to keep it from developing a skin. Set it in the refrigerator to chill for at least 2 hours.

Make the cupcakes while the pudding chills. Take two cupcake trays and line 16 of the wells with paper liners. Pre-heat the oven to 350 and set up a stand mixer with the paddle attachment. Whisk the flour, baking powder, cinnamon and salt together in a bowl to aerate the dry ingredients and then set them aside. Combine the butter and sugar in the stand mixer bowl and beat them together until fluffy. Add in each egg one at a time, followed by the two extracts. Turn the speed to low and slowly add in the dry ingredients until you have a sticky, thick batter. Evenly distribute the batter among the 16 wells, filling them just about 3/4 of the way. Bake the cupcakes for about 20 minutes, until golden and crackly around the edges. Let them cool completely.

Make the frosting while the cupcakes bake and cool. Wash out the stand mixer bowl and paddle attachment first. Then combine the cream cheese and butter in the bowl and beat them together thoroughly. Add in the cinnamon and banana extract next. Then turn the speed to low and slowly add in the powdered sugar. Cover the bowl and refrigerate the frosting until you are ready to assemble the cupcakes. When you are ready to assemble the cupcakes, mash the banana for the pudding first. Fold it into the rest of the pudding to make it thicker and more flavorful.

Use a 1 inch circle cutter to cut out a hole in the center of each cupcake, being careful to not go all of the way to the bottom. Spoon the pudding into the holes generously to fill the cupcakes. Scoop the frosting into a piping bag fitted with a star tip and frost each cupcake. Then take 8 of the vanilla wafers and put them into a zip top bag. Crush them into crumbs with a rolling pin, then sprinkle each of the cupcakes generously with the crumbs. Finish by sticking a whole vanilla wafer on top. There will be leftover crumbs and pudding that can be made into great dessert later! Store the cupcakes in a sealed container in the refrigerator until you are ready to serve them. Enjoy!