Preheat the oven to 350°F (175°C). Line two standard muffin tins with paper liners.
Whisk the flour, baking soda, cinnamon, and salt in a medium bowl. Set aside.
Beat the butter, brown sugar, and granulated sugar with a hand or stand mixer on medium speed for 3 minutes until pale and fluffy.
Add the eggs one at a time, beating for 30 seconds between each. Mix in the mashed bananas, sour cream, and vanilla until combined.
Add the dry ingredients in 3 additions, alternating with the buttermilk in 2 additions (flour → milk → flour → milk → flour). Mix on low speed until just combined after each addition. Do not overmix.
Scoop the batter into the cupcake liners, filling each ¾ full (about ¼ cup per cupcake).
Bake for 18–20 minutes, until the tops spring back and a toothpick comes out clean or with a few moist crumbs.
Cool in the pan for 5 minutes, then transfer to a wire rack. Cool completely for at least 45 minutes before filling or frosting.
Make the frosting: Beat the butter and cream cheese on medium speed until smooth, about 2 minutes. Add the salt and cinnamon. Gradually add the powdered sugar on low speed. Add the vanilla, then beat on medium-high for 2 minutes until silky and pipeable.
Core each cooled cupcake using a cupcake corer or small knife, about ¾ inch wide and ¾ inch deep.
Fill each cupcake with cold banana pudding using a piping bag until level with the cupcake surface.
Frost with cream cheese frosting using a large star tip. Top each cupcake with a dehydrated banana chip.
Refrigerate for 20 minutes before serving to let everything set.