Preheat the oven to 350°F (177°C) and line 2 baking sheets with parchment paper. You want parchment here because it helps the cookies spread evenly without sticking.

Whisk the flour, baking soda, cinnamon, pumpkin pie spice, salt, and oats in a large bowl. The dough should look “oaty” and evenly spiced before any wet ingredients go in.

Blot the pumpkin: Measure 1 cup pumpkin purée, then press it between paper towels until it looks noticeably drier and less glossy. This is where the texture changes—less free water means a cookie-like chew rather than a cakey lift.

In a medium bowl, whisk melted butter, maple syrup, brown sugar, and granulated sugar until glossy. Then whisk in the egg yolk, blotted pumpkin, and vanilla until smooth.

Pour water into the dry mix until the dough looks evenly hydrated and starts to pull away from the bowl. Stop when you no longer see dry flour pockets—overmixing here makes the dough pasty instead of chewy.

Fold in chocolate chips. If you want bakery-style tops, save a small handful to press onto the scoops before baking.

Scoop about 1.5 tablespoons of dough per cookie onto baking sheets, spacing them apart. Lightly flatten each scoop so the spread is predictable (this dough can dome if you don’t).

Bake 11–13 minutes, until edges look set and lightly browned while centers still look soft. Let cookies cool on the sheet for about 10 minutes before moving—this is when they finish setting without drying out.