Preheat oven to 325 degrees. Line a cookie sheet with parchment paper.
Cut butter into small pieces and place in a medium sized bowl or the bowl of a stand mixer.
Add both the ¼ cup and 2 tbsps of brown sugar. Beat until light and fluffy (about 2 minutes).
Add vanilla extract and molasses. Beat until combined.
Add flour ¼ cup at a time, mixing well between additions.
Continue to beat until the dough starts to clump together.
Using your hands take dough out of the bowl and push together to make one large dough ball.
Pinch off about a tablespoon of dough and roll into a ball.
Place dough balls on baking sheet and using the bottom of a cup, flatten out the dough ball to desired thickness.
Bake for 15-17 minutes or until edges begin to become golden.
Remove cookie sheet from oven and allow cookies to cool on the cookie sheet.