In a medium bowl, whisk together flour, cocoa powder, baking powder, baking soda, cream of tartar, kosher salt, and optional espresso powder. Set aside.
In the bowl of a stand mixer fitted with a paddle attachment, beat butter and sugar on medium speed until smooth, about 2 minutes. Add egg and vanilla. Mix for another 2 minutes until well combined. Scrape down sides of bowl to ensure thorough mixing.
Reduce to low speed. Add flour mixture in two additions. Mix until just combined, when there are no longer any dry streaks of flour. Scrape down sides of the bowl. Fold in chocolate chunks.
Use a size 40 scoop (1 ½ Tbsp scoop) to portion out the cookie dough into 21 pieces.
Place cookie dough on parchment lined baking sheet or plate. Cover with plastic wrap. Chill in the fridge for at least 2 hours, or up to overnight.
Preheat oven to 350°F. Place chilled cookies on parchment lined baking sheet, spacing them about 2-inches apart.
Bake in the center rack of oven for 10-12 minutes, rotating sheet midway through baking. Immediately sprinkle cookies with sea salt flakes. Leave cookies on baking sheet for 3 minutes. Use a mini offset spatula or cookie spatula to transfer cookies to wire rack. *It is better to err on the side of under-baking.