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Coarsely chop cookies in a food processor. Set aside.
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Whisk egg, condensed milk, cocoa, cornstarch and salt in a heavy saucepan until smooth. Gradually whisk in milk. Bring to a boil over medium-low heat, whisking constantly, until thickened, 7 to 9 minutes.
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Remove from heat; add chocolate and vanilla, whisking until the chocolate melts. Transfer to a bowl. Place plastic wrap directly on the surface to prevent a skin from forming. Refrigerate until ready to serve.
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To assemble dirt cups, divide the pudding between four 1/2-cup containers. Top each container with one heaping tablespoon of cookie crumbs and 1 strawberry.
Tips
Tip: For a variation, cut strawberry into small cubes and place between layers of pudding.
To make ahead: Prepare through Step 3 and refrigerate pudding for up to 3 days.