Place chopped chocolate into a large, heatproof bowl. Set a fine-mesh sieve over the bowl.
In a medium, heavy-bottomed saucepan, whisk together the Redpath® Dark Brown Sugar, cornstarch, cocoa powder, and salt. Whisk until evenly combined and no lumps remain. Add 1 cup (250 ml) milk, whisking until smooth, and lump-free. Slowly whisk in the remaining milk.
Place saucepan over medium to medium-high heat, whisking constantly but gently to prevent lumps from forming until just a few bubbles break the surface. Reduce heat to medium-low. Use a heatproof rubber spatula to scrape down the bottom and sides of the pan, if necessary. Continue whisking and cooking for 3 minutes or until mixture is thick enough to coat the back of a spoon (see Chef’s Tips). Immediately, remove from heat and pour the hot mixture through the sieve and into the bowl of chopped chocolate, using the heatproof spatula to gently press the pudding through. Discard any lumps.
Cover bowl with a lid or large plate. Let sit for 2 minutes.
Uncover and gently whisk until the chocolate melts and pudding is smooth (see Chef’s Tips). Whisk in the pure vanilla extract.
To prevent a skin from forming on the top of the pudding, place a piece of plastic wrap or parchment paper directly onto the surface of the pudding. Store in the refrigerator and chill for at least 30 minutes or until the pudding is at least room temperature.
Carefully remove the plastic wrap or parchment paper from the pudding. Scrape any pudding from the wrap/paper back into the bowl. Sprinkle the remaining chocolate cookie crumbs into the pudding. Fold the crumbs into the chilled pudding.
Transfer the pudding to a 1 ½ quart / 6 cup clear dish so that the layers are visible (see Chef’s Tips).
Place a piece of plastic wrap or parchment paper onto the surface of the pudding to prevent a skin from forming and place back into the fridge to chill and thicken; at least 4 hours or overnight.
Just before serving, sprinkle the cocoa-dusted cookie crumbs over the entire surface of the chocolate pudding. Insert or press the edible flowers or herbs into the pudding to mimic a mini garden.