|Preheat oven to 325 degrees. Line two large baking sheets with parchment paper.
Whisk the flour, baking soda, salt and cinnamon together in a medium bowl. Set aside.
Use an electric mixer to cream together butter and sugars until well blended. Beat in the egg, yolk, and vanilla until combined. Add in the dry ingredient mixture and beat on low speed until just combined. Carefully stir in the caramel bits and diced pears until combined.
Use a small cookie scoop or a spoon to form the dough into tablespoon-fulls. Place on a cookie sheet at least 2.5 inches apart, and then dot on top with a few additional caramel bits. Bake cookies until the outer edges are golden and begin to slightly harden, about 15 minutes. Remove and let the cookies cool on the baking sheets.