Gather all necessary ingredients before beginning the preparation process.

Cook the dried tapioca pearls according to the instructions on the package. Once cooked, set them aside for later use.

To make the brown sugar syrup, combine the dark brown sugar and water in a saucepan. Heat over high heat until the mixture begins to boil. Reduce the heat to medium and let it simmer gently for about 5 minutes, stirring occasionally. The syrup should thicken slightly during this time and will continue to thicken as it cools.

Transfer the prepared syrup to a bowl and allow it to cool to room temperature. For convenience, this syrup can be made ahead of time and stored in the refrigerator overnight.

Pour half of the cooled brown sugar syrup into a squeeze bottle. Use the bottle to drizzle the syrup along the inside walls of a milkshake glass, creating decorative "stripes."

Spoon 1/4 cup of the cooked tapioca pearls into the prepared glass.

In a cocktail shaker, combine the milk and 1 tablespoon of the brown sugar syrup. Adjust the amount of syrup to suit your desired sweetness level. Add a handful of ice to the shaker, then shake vigorously until the mixture becomes frothy and well-chilled.

Carefully strain the frothy brown sugar milk into the syrup-lined glass. Serve immediately with a wide bubble tea straw or smoothie straw for an authentic experience. Enjoy the refreshing sweetness of homemade bubble tea!