Preheat the oven to 350° (F). Grease a 9-inch baking dish and line with parchment paper.
In a small bowl add ¼ cup brewed Choffy grounds and cover just to the top with brewed Choffy. Set aside for 5 minutes.
In a large bowl, combine the brownie mix, egg, ¼ cup brewed Choffy, and Choffy grounds. Mix until well-blended. About 50–60 strokes. Spread into a prepared baking dish.
Bake in preheated oven until a toothpick inserted 1-inch from the edge of pan comes out clean. 30–35 minutes. Remove from the oven and let cool completely, about 30 minutes.
Cut the cooled brownies into ½-inch squares and set aside.
In the bowl of your stand mixer, add heavy whipping cream. Whip on high until stiff peaks form. Add powdered sugar, almond extract, and vanilla extract. Chill in the refrigerator while you prepare the chocolate pudding mousse.
In a large bowl, combine the condensed milk, the remaining ½ cup of Choffy, and pudding mix. Mix until smooth. Fold in 2 cups of whipped cream until no streaks remain.
In two pipping bags, or 2 gallon Ziploc bags, fill one with chocolate mousse mixture, and one with whipped cream. Cut the tip off each bag.
Place a layer of brownies on the bottom of each mason jar. Followed by a layer of piped chocolate pudding mixture, a layer of cherry pie filling, and a piped layer of whipped cream. Repeat with a layer of brownies, chocolate pudding, and end with cherry pie filling. Place the lid on each mason jar and chill for 8 hours. Save the remaining whipped cream to top off each trifle at the time of serving.