Warm the milk to 110–115°F (about as warm as a hot bath — not steaming).
Sprinkle the yeast over the milk and whisk gently.
Let it sit for 5 minutes, or until the top looks foamy and bubbly.
If it doesn’t foam, your milk may have been too hot or too cold — start over for best results.
Mix the Dough
Add the eggs, softened butter, granulated sugar, and salt into the bowl with the yeast mixture.
Mix until mostly combined — it’s okay if the butter stays a little lumpy at this stage.
Add 3 1/2 cups of the flour and banana pudding mix to the bowl.
Fold the dry ingredients into the wet until just combined.
Let the dough rest for 5 minutes (this helps the flour hydrate and makes kneading easier).
Knead the Dough
Knead by hand or with a mixer and the hook attachment for 5–7 minutes, adding the last 1/2 cup of flour.
The dough should become soft, smooth, and slightly tacky but not overly sticky.
If it sticks heavily to your hands, sprinkle in 1 tablespoon of flour at a time until it’s manageable.
Shape into a ball and place it back in the bowl.
First Rise
Cover the bowl with a clean towel or plastic wrap.
Let the dough rise for 30 minutes, or until noticeably puffier (it may not double yet — that’s okay).
Place the bowl somewhere warm, like on top of the oven while it preheats or near a sunny window.
Make the Banana Cinnamon Filling
In a small bowl, mix the softened butter, brown sugar, cinnamon, and vanilla. Stir until thick and smooth.
Smash the banana until mostly smooth with small bits remaining, then fold it into the cinnamon mixture until fully combined.
Set aside.
Roll Out the Dough
Lightly flour your counter.
Roll the dough into a large rectangle (about 12×18 inches).
Spread the banana cinnamon filling evenly all over the dough, reaching all the way to the edges for even flavor.
Shape the Rolls
Starting from the long side, roll the dough tightly into a log.
Use a sharp knife or unflavored dental floss to slice into 12 large rolls.
Alternatively, slice the unrolled dough with a pastry cutter or pizza cutter into 2 1/2 inch wide slices. Then roll each slice individually for the perfect swirl.
Transfer the rolls into a greased 9×13-inch baking dish.
Salted Caramel
Add the white sugar to a medium saucepan over medium heat. Let it melt undisturbed until the edges liquefy, then gently swirl the pan until fully melted and deep amber in color.
Carefully add the butter, cubed and whisk continuously until melted and fully incorporated.
Remove from the heat and slowly pour in the heavy cream while whisking (the mixture will bubble vigorously), then continue stirring until smooth.
Stir in the salt. Let cool slightly before using so it thickens.
Second Rise
Cover the rolls and let them rise for 20 minutes.
They should look puffier and fill more of the pan.
Cream Pour + Bake
Pour about 1/2 cup of the caramel sauce around the edges of the rolls, so the bottoms come out coated in caramel.
Gently pour the heavy cream over and around the rolls — this helps them bake extra soft and gooey.
Bake at 375°F for 25–30 minutes, or until the tops are lightly golden but still soft.
Don’t overbake or they’ll lose their gooey texture.
Make the Vanilla Glaze
In a mixing bowl add the powdered sugar and milk. Whisk until smooth.
While the rolls are still baking, add thin slices of 1/2 a banana to the rest of the caramel sauce, and reheat on medium low to slightly cook the bananas into the caramel for about 3-5 minutes.
Glaze the Rolls.
As soon as the rolls come out the oven, spread the vanilla glaze all over them.
Finish by pouring the bananas and caramel all over the rolls.