Preheat the oven to 350 °F (180 °C). Line a large baking sheet with non-stick parchment paper. Set aside.

Add the pumpkin seed to a high-speed blender. Blend on medium-high speed, stop a few times, scrape down the sides of the jug, and repeat until finely ground with barely any large pieces of seeds.

Pour the ground pumpkin seed into a mixing bowl and add the remaining ingredients: maple syrup, and vanilla extract.

Stir with a rubber spatula until it forms a sticky cookie dough.

Oil your hands generously because the dough sticks. Grab a tablespoon of cookie dough, roll it into a ball, and release it on the baking sheet. Press the center with an oil-finger tip, or the back of an oiled teaspoon, to slightly flatten the ball, and create a cavity in the center of the cookie.

Repeat with the remaining cookie dough, placing the cookies an inch apart from each other on the baking sheet.

Bake the cookies for 12-14 minutes at 350°F (180°C) until just golden brown on the edges.

Let the cookies cool down for 30 minutes on the baking sheet at room temperature, then transfer them to a cooling rack.

In a microwave-safe glass bowl, add chocolate chips and oil. Microwave for 30-second bursts, stir between bursts, and repeat until the mixture is fully melted.

Use a teaspoon to fill each baked cookie thumbprint with the melted chocolate.

Pop the plate in the fridge for 30 minutes or until the chocolate filling firms up.