In a medium bowl, beat the softened cream cheese, maple syrup, and vanilla extract with an electric mixer until smooth, then add the Greek yogurt and mix on low speed until creamy and combined.

Pour the cooled coffee into a shallow bowl and break the ladyfingers into pieces that fit inside four 6- to 8-ounce serving glasses.

Quickly dip half the ladyfinger pieces into the coffee, about 1 second per side, divide them among the four glasses, and spoon half the Greek yogurt filling over them.

Dip the remaining ladyfingers into the coffee and divide them among the glasses, then top with the remaining filling and smooth the tops.

Cover and refrigerate for at least 4 hours, or overnight, until the cookies soften and the filling sets.

Dust with cocoa powder just before serving.