Add the warm milk and banana to a large mixing bowl. Sprinkle on the yeast and let sit until it begins to foam.
Stir in the flour, melted butter, cinnamon, and salt. Continue stirring until a dough is formed and pulls away from the sides of the bowl.
Place the dough on a well floured work surface and knead by hand for about 5 minutes. Form the dough into a ball and set aside.
Clean the large mixing bowl and add the oil. Place the dough ball in the bowl and flip around a couple times to coat in the oil. Loosely cover the bowl and set in a warm place until about doubled in size, about 1 hour.
Preheat oven to 350°F. Butter the inside of an 8x8 baking dish with 1 TBSP of softened butter.
In a small bowl mix together the filling ingredients and set aside. On a lightly floured surface, roll out the dough into a long rectangle (roughly 16x12 inches), short-side facing you, about 1/4-inch thick. Spread the filling evenly on top of the dough. Roll the dough tightly into a log and lay seam side down. Using a serrated knife carefully cut sections about 2-inches wide for a total of 6 rolls. Using a spatula carefully lay the rolls in the buttered baking dish cut-side up and bake in the preheated oven until lightly golden brown, about 30 minutes.
Place the sliced banana and heavy cream in a food processor and pulse until smooth and thickened, about 1 minute.
Take the rolls out of the oven and allow to cool for about 10 minutes. Spread the banana cream mixture on top of the rolls.
Serve right away or cover, refrigerate and warm up for later.
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