Preheat the oven to 325 degrees. Line 2 baking sheets with parchment paper.

Combine the flour, cocoa powder, chili powder, cinnamon, salt, and baking powder in a mixing bowl and whisk to combine.

Combine 1 cup semisweet chocolate chips with the butter in a microwave-safe bowl and microwave for about 1 minute or until the chocolate is melted. Stir to combine.

Remove the stems from the cherries, coarsely chop, and pat dry with paper towels. Place in a bowl and combine with the remaining 1 cup semisweet chocolate chips, the bittersweet chocolate chips, and the pumpkin seeds.

Using an electric mixer, preferably fitted with a paddle attachment, beat the eggs and sugar on medium-high speed for a full 5 minutes. Beat in the vanilla. Turn the mixer to medium-low and mix in the melted chocolate and butter mixture.

Using a spatula, fold in the flour mixture, making sure to fully combine. Add the cherries, chocolate chips, and pumpkin seeds and fold in until fully combined.

Using a small ice cream scoop or a tablespoon, mound the cookies on the prepared baking sheets, about 2 inches apart. Gently press down each cookie to flatten slightly.