Bloom the yeast by combining warm milk (105-110°F), 1 tablespoon sugar, and yeast; let stand 5-10 minutes until foamy.
Add eggs, remaining sugar, vanilla, and cinnamon to the yeast mixture. Add flour and salt; mix on low until incorporated, then medium for 3 minutes until dough comes together.
With mixer on medium-low, add softened butter piece by piece. Continue mixing 6-8 minutes until dough is smooth, elastic, and pulls away from bowl sides.
Knead dough by hand 2-3 minutes on a lightly floured surface until soft and pliable. Shape into a ball and place in a greased bowl.
Cover and let rise in a warm spot for 1-1.5 hours until doubled in size.
Make the topping by creaming shortening and powdered sugar until smooth. Mix in vanilla and flour to form a soft, playdough-like consistency.
Divide dough into 12 equal pieces (about 80-85g each). Shape each into a smooth, taut ball and place on parchment-lined baking sheets, 3 inches apart.
Divide topping into 12 pieces. Flatten each between plastic wrap into a 3-3.5 inch round disc. Drape over each dough ball, pressing firmly to adhere.
Score the shell pattern into each topping using a concha stamp or sharp paring knife. Press firmly but don't cut through to the dough.
Cover loosely and let rise for 45 minutes to 1 hour until puffed. Preheat oven to 375°F (190°C) during the last 15 minutes.
Bake for 16-18 minutes until tops are set and bottoms are lightly golden. Cool on baking sheet 5 minutes, then transfer to a wire rack.
Cool completely for at least 20 minutes before serving. The topping sets into a crisp, crumbly shell as it cools.