Whisk sugar, cornstarch, cocoa, and salt in a medium pan. Combine cream, milk, and vanilla in a large measuring cup. Whisk 2 cups liquid into dry ingredients until cornstarch is completely dissolved. Whisk in remaining cream mixture until smooth.
Place pan over medium heat. Cook, whisking constantly, until mixture comes to a boil and thickens, 7 to 8 minutes. Add chocolate; cook, whisking until melted, about 1 minute. Remove from heat; whisk in butter until melted. Divide pudding between glasses, leaving about 1/2 inch at the top. Refrigerate until completely set, about 1 hour; chill until ready to serve.
Just before serving, top each with 1 1/2 teaspoons crushed cookies, and "plant" an herb sprig. Serve cold.
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