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1. Place the cocoa and ¾ cup of the half-and-half in a small bowl and mix with a fork until well blended. Add more half-and-half if needed to form a smooth paste.
2. Place the espresso powder, sugar, and the remaining half-and-half in a medium heavy-bottomed saucepan.
3. Add the chocolate paste to the coffee mixture, mix well, and bring to a simmer.
4. Remove from the heat and add the vanilla. Cool to room temperature.
5. Fill popsicle molds according to the manufacturer’s instructions.
6. Place in the freezer for 4–6 hours.
7. Remove popsicles from the freezer and hold them under hot running water for 5–10 seconds until their molds release. Enjoy immediately.
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