Special equipment: four 8-ounce Mason jars
Combine the cream cheese, orange juice concentrate, sugar and vanilla in a large bowl and begin to beat with an electric mixer on medium-low speed, increasing the speed as the mixture comes together and is smooth, about 1 minute. Add the heavy cream and beat, increasing the speed to medium-high until soft peaks form, about 2 minutes.
Set aside 4 mandarin orange segments for garnish. In each Mason jar, place 2 cookies in one layer in the bottom. Break one of the cookies to fill any large gaps. Next, spread 2 tablespoons of the whipped cream mixture in each jar, topped by 3 to 4 mandarin segments in each. Repeat the layering with 2 more cookies, 2 tablespoons cream and 3 to 4 mandarin orange segments per jar 2 more times, for a total of 3 layers. For the very top layer of mandarin segments, instead of 3 to 4 pieces, garnish with a single reserved mandarin orange segment.
Refrigerate for at least 6 hours and up to 12 hours to allow the cookies to soften.
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