Prepare the dough: Start by creaming the softened butter, brown sugar, and granulated sugar together in a large mixing bowl until smooth and fluffy. Add the eggs, one at a time, mixing well after each addition. Stir in the vanilla extract and molasses until fully combined.
Add the dry ingredients: In another bowl, whisk the flour, baking soda, cinnamon, and salt together. Gradually add the dry mixture to the wet ingredients, mixing until just combined. Fold in the oats gently with a spatula, ensuring an even distribution. The dough will be sticky, but that’s normal. Add the chopped soft caramels, stirring just enough to incorporate them.
Chill the dough: Cover the dough with plastic wrap and chill it in the fridge for at least 40 minutes. This step is essential for making the sticky dough easier to handle and for enhancing the flavor and texture of the cookies.
Form the cookies: Preheat your oven to 350°F (175°C). Line your baking sheets with parchment paper to prevent sticking. Use a traditional ice cream scoop or measure out about 3 tablespoons of dough for each cookie. Roll the dough into balls and place them 2 inches apart on the prepared baking sheets.
Bake to perfection: Bake one sheet at a time in the center rack of the oven for 13 minutes. The cookies may not look fully done, but trust the timer! The edges should be lightly golden while the centers remain soft.
Cool completely: Remove the cookies from the oven and allow them to cool on the baking sheet for 5 minutes before transferring them to a wire rack. This helps their texture and structure develop, giving you crisp edges and a perfectly chewy center. Sprinkle with flakey sea salt while they are still warm.