Preheat oven to 350 degrees F. Liberally grease 4 ramekins with cooking spray and set atop of a baking pan. Set aside.
Roll out the crescent roll sheet on a clean work surface, stretching out into a thin-ish rectangle. Brush with melted butter all over and sprinkle evenly with the brown sugar and cinnamon.
Begin rolling the dough, long side away from you, into a tight roll. Pinch the seams to seal. Using a sharp serrated knife or unflavored dental floss, cut the roll into 14 equal pieces, discarding the end pieces.
Place three cinnamiddles into the greased ramekins. Bake for approx. 10-15 minutes or until gooey and dough is light golden brown. Cool for about 5 minutes.
While cinnamiddles bake, make your brown sugar sauce. In a small saucepot over medium heat, bring the butter and brown sugar to a simmer. Remove from heat and evenly distribute the sauce among the ramekins when they're finished baking.
To make the glaze, whisk together the softened cream cheese, vanilla, cream and powdered sugar until a pourable, glossy glaze is achieved. Pour over the cinnamiddles.