Preheat the oven to 375 degrees Fahrenheit and lightly grease a large cookie sheet.
In a large bowl, add in the softened coconut oil and both sugars, whisking everything until well combined and the mixture looks smooth and well combined. Add in the molasses, applesauce, and vanilla, whisking them together until combined.
Add in the flour, baking soda, salt, and pinch of cinnamon, mixing everything together using a rubber spatula until the mixture becomes wet, thick, and holds together well. Fold in chocolate chips.
Using a medium-size scoop (about 1 ½ Tbsps), scoop each cookie dough onto the prepared cookie sheet, leaving 1-inches between each cookie for spreading when they bake.
Bake for 11 to 12 minutes, or until the edges are golden brown.
OPTIONAL: At 5 minute mark (cookies should be slightly puffed in the center), lift baking sheet and let it drop against the rack. Repeat about twice if needed. This allows the edges to set and the inside to fall down.
Remove the cookies from the oven and press remaining chocolate chips on top of warm cookies, if desired.
Cool cookies on the cookie sheet for a few minutes before serving. Enjoy with your favorite glass of dairy-free milk.