Preheat your indirect smoker to 300 degrees F. This method is also adaptable for the oven, if you don't own a smoker.
Slice the sausage into 1/2 inch thick rounds. Wrap each slice of sausage with a half of a slice of bacon so it forms a little "shot glass" of meat. Season the shots with the sweet rub.
In a medium bowl, beat together the cream cheese, brown sugar, and most of the pineapple chunks, reserving a couple of tablespoons of the pineapple to top the shots with later.
Transfer the cream cheese mixture to a quart sized sip top bag and snip off the bottom corner. Fill each shot glass with some of the mixture, leaving just a little room at the top. Spoon the remaining crushed pineapple into the top of each shot and season them all again with a little more sweet rub.
Carefully transfer the shots to the grill grates (or a foil lined pan if using your oven) and cook for 75-90 minutes, or until the bacon gets crisp. Serve warm with plenty of napkins and enjoy!