Bring 2 cups water to a boil in a small saucepan. Add tapioca pearls and stir gently until they begin floating to the top. Reduce heat to medium and simmer until softened and dark, about 25 minutes. Remove from heat, cover, and let sit for 15 minutes.

Meanwhile, bring 2 cups water to a boil. Remove from heat and add tea leaves. Let steep for 15 minutes. Strain out tea leaves and refrigerate tea.

Drain pearls. Bring 1/4 cup water to a boil in the empty saucepan. Stir in brown sugar until dissolved. Immerse pearls in syrup and let sit until room temperature, about 15 minutes

Divide pearls and desired amount of syrup between 2 tall glasses. Pour in tea.

Add ice, milk, and sweetened condensed milk to both glasses. Stir before drinking.