In a medium sized pan, add butter, rum, brown sugar, vanilla extract, and cinnamon. Mix with a whisk or spoon. Bring to a slight boil then turn off the heat.

Remove from heat and allow to cool for 20 minutes.

In the bowl of a mixer, beat heavy cream on high speed until soft peaks develop. Add in confectioners sugar and continue to beat until stiff peaks develop. Remove whipped cream from the bowl and place in a separate bowl. Then put the mixture in the refrigerator.

Clean bowl then add cream cheese and beat on high until nice and fluffy.

Slowly add in sweetened condensed milk, milk, banana pudding mix, vanilla pudding mix, and vanilla extract. Beat until well incorporated. Stop in between mixing ingredients to use a spatula to mix in the food on the sides of the bowl. The pudding at this point should not be too thick. It should be “spreadable”. If it seems too thick add in more cold milk, starting at 2 ounces (¼ cup).

Remove whipped cream from the refrigerator and slowly fold half of whipped cream into the banana pudding.

Arrange a full row of ladyfingers on the bottom of a 9x13 sized baking pan. Pour 1/4 of warm rum sauce over ladyfingers to soak them.

Next add slices of 2 bananas over the ladyfingers and pour another 1/4 of warm rum sauce over bananas.

Take half of the banana pudding cheese mixture and smooth over the top of the sliced bananas. Again, the banana pudding mixture should be “spreadable” and not too thick. See notes above for thinning the mixture if needed.

Next create another layer by repeating all steps starting with adding another row of ladyfingers, pouring rum sauce on ladyfingers, adding sliced bananas, pouring remaining rum sauce and finally add the rest of the banana pudding mixture.

Lastly, take the remaining half of whipped cream and spread it over the top of the tiramisu.

Finish the top of the tiramisu with crumbled wafers over whipped cream.

Place the baking pan in the refrigerator for at least 3-4 hours before serving.