In a high-speed blender, combine the plain Greek yogurt, maple syrup, vanilla extract, your choice of milk, chia seeds, instant espresso powder, and a pinch of salt. Blend on medium-high for about 60 seconds or until smooth and creamy.

Carefully pour the blended pudding mixture into four sealable jars, dividing it evenly. Leave space at the top for toppings and seal the jars. Refrigerate for at least 2 hours or overnight.

In a medium bowl, whisk together the additional Greek yogurt, maple syrup, and vanilla extract until smooth and creamy. Set aside.

Dollop the yogurt mixture onto each jar of pudding, smoothing out the top. Dust generously with cocoa powder.

Cover the jars again and return to the refrigerator for at least an hour to allow the flavors to mingle, preferably overnight.

Serve the jars chilled, optionally swirled with additional cocoa powder.