01 - Preheat the oven to 350°F. Line two baking sheets with parchment paper.
02 - In a medium bowl, whisk together flour, baking soda, cinnamon, and salt until well blended.
03 - In a large bowl, beat softened butter, brown sugar, and granulated sugar until light and fluffy, about 2-3 minutes.
04 - Beat in eggs one at a time, then mix in vanilla extract until fully incorporated.
05 - Gradually add dry ingredients to the wet mixture, mixing just until combined. Fold in oats and raisins until evenly distributed.
06 - Drop tablespoonfuls of dough onto prepared baking sheets, spacing about 2 inches apart.
07 - Bake for 10-12 minutes, until edges are golden and centers are set. Do not overbake.
08 - Let cookies cool on baking sheets for 5 minutes, then transfer to wire rack to cool completely.
09 - Melt butter in a medium saucepan over medium heat. Stir in brown sugar and milk; bring to a gentle boil, stirring constantly. Boil for 2 minutes, then remove from heat. Cool slightly for 2-3 minutes, then whisk in powdered sugar and salt until smooth.
10 - Frost each cooled cookie with a generous layer of caramel frosting. Let set before serving.