Preheat the oven to 350°F (175°C). Line two baking sheets with parchment paper or a silicone baking mat and set aside.
Whisk the peanut butter and maple syrup together in a large mixing bowl until smooth. Add the egg and vanilla, then whisk until the mixture is glossy and homogenous.
In a separate bowl, stir together the oats, oat flour, baking soda, salt and cinnamon until evenly combined. Breaking up any oat clumps will help the dough come together more easily.
Pour the dry mixture into the wet ingredients and fold with a spatula just until combined — the dough will be thick and sticky. Fold in the chocolate chips by hand so they distribute without overworking the batter.
Chill the dough briefly: cover the bowl and refrigerate for 10 minutes to firm up slightly (this keeps the cookies from spreading too much and helps achieve a chewy center).
Portion the dough into roughly 1 1/2 tablespoon-sized mounds (a small cookie scoop works well) and place them 2 inches apart on the prepared baking sheets. Lightly press each mound with the back of a spoon or fork to flatten about 1/2 inch thick.
Bake one sheet at a time in the center of the oven for 9 to 11 minutes, until the edges are set and the bottoms are lightly golden. The centers will still look soft — that’s what keeps them chewy.
Remove cookies from the oven and immediately sprinkle a tiny pinch of flaky sea salt over each cookie if desired. Let them cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
Store cooled cookies in an airtight container at room temperature for up to 4 days, or freeze for longer storage.