01 - Preheat the oven to 350°F. Line two baking sheets with parchment paper for even baking.
02 - In a medium bowl, whisk together flour, baking soda, cinnamon, and salt until evenly mixed.
03 - Using an electric mixer, beat the softened butter, brown sugar, and granulated sugar until the mixture is light and fluffy.
04 - Add eggs one at a time to the creamed mixture, blending well after each addition. Stir in vanilla extract.
05 - Gradually add the dry ingredient blend to the wet mixture, stirring gently until just combined.
06 - Fold in the rolled oats and raisins carefully, ensuring even distribution throughout the dough.
07 - Drop rounded tablespoons of dough onto the prepared baking sheets, spacing each about 2 inches apart to allow for spreading.
08 - Bake for 11 to 13 minutes or until the edges have a light golden color while centers remain slightly soft.
09 - Allow the cookies to cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely.
10 - In a small saucepan, melt butter over medium heat. Stir in brown sugar and milk; bring to a gentle boil and cook for 2 minutes, stirring constantly.
11 - Remove saucepan from heat and let cool for 3 minutes. Whisk in powdered sugar and a pinch of salt gradually until smooth and spreadable.
12 - Spread the caramel frosting evenly over the cooled cookies. Allow the frosting to set before serving.