Heat oven to 350°F. Line two baking sheets with parchment.
Toss the chopped gumdrops with 1 tbsp flour until lightly coated; set aside.
Whisk flour, baking soda, baking powder, salt, and cinnamon in a bowl.
Cream butter, granulated sugar, and brown sugar until fluffy, about 2 minutes.
Beat in eggs one at a time. Mix in vanilla and milk until smooth.
Stir in dry ingredients on low just until a soft dough forms; do not overmix.
Fold in floured gumdrops and pecans, distributing evenly.
Scoop rounded tablespoons of dough onto sheets, spacing about 2 inches apart.
Bake 9–11 minutes until edges are set and lightly golden; centers will look soft.
Cool on the sheet 5 minutes, then transfer to a rack to finish cooling.