Preheat oven to 375 degrees.
Brush the metal sauce cups with canola oil and wrap a slice of thick-cut bacon snugly around the metal cup with the fat side down.
Place the bacon-wrapped metal cup upside-down on a silicone mat set on a baking sheet.
Secure the bacon to the cup using a length of butcher's twine.
Place the bacon on the center rack and cook until the bacon is cooked through and just crispy.
Take the bacon out of the oven and let it cool until it is safe enough to handle.
Cut the twine, and if necessary, gently run the sharp blade of a paring knife under the bacon to separate it from each cup.
Place the bacon rings on a plate and discard only rendered fat from the baking sheet.
Invert the bacon cups with their narrow end down on the baking sheet, and place a tablespoon of shredded cheddar cheese into the bottom of each bacon ring.
Place the sheet pan back into the still-warm oven and reduce the heat to 200 degrees. Allow the cheese to melt; this should only take a few minutes.
Remove the bacon from the oven and allow them to cool.
Spoon mashed potatoes into a zip-lock bag and press the contents to a corner of the bag, using a sharp pair of kitchen shears to cut off a lower corner.
Pipe the mashed potatoes into the bacon cups, and press (2) 2-inch cut French green beans into the potatoes at opposing angles.
Top each appetizer with a tsp of the cranberry and maple syrup mixture.
Serve warm.