In a large measuring cup, combine the milk, coffee, ¼ cup of maple syrup, and 1 ½ teaspoons of vanilla. Divide the mixture among 4 jars or airtight containers.
Stir ½ cup of oats and 2 teaspoons of chia seeds into each container, ensuring the oats are submerged in liquid. Cover and refrigerate for at least 4 hours or up to 12 hours.
In a medium bowl, whisk the cream cheese until smooth. Whisk in the yogurt, the remaining 2 tablespoons of maple syrup, and the remaining 1 teaspoon of vanilla until well combined and creamy.
Spoon the yogurt mixture over the oats, spreading into a smooth layer. Dust with cocoa powder and serve chilled.
