Cream together softened butter and sugars on medium speed until creamy. About 2 minutes.
Add eggs, vanilla and molasses to the bowl and continue beating until everything is fully combined. Scrape the sides of the bowl with a spatula as needed.
In a separate bowl combine flour, baking soda, salt and cinnamon.
Slowly add the dry ingredients to the wet and beat on low until everything is incorporated. Scrape the sides of the bowl with a spatula as needed.
Add oats one cup at a time and stop mixing as soon as the dough comes together. It will be very sticky.
Refrigerate for 40 minutes.
Preheat oven to 350 degrees.
Line large baking sheets with parchment paper.
Using a traditional size ice cream scoop, scoop cookie dough out and place on the sheet pans. If you don't have an ice cream scoop, measure out 3 tablespoons per cookie, form in a ball and place on the cookie sheets.
Unwrap 40 Werther's sot caramels and press 2 in the center of each cookie.
Bake in rounds with only one pan in the oven at a time on the middle rack for 13 minutes.
Remove and immediately top each cookie with a sprinkle of flakey sea salt.
Allow to cool and set for 30 minutes on the counter.