Start by draining the maraschino cherries. Keep that cherry juice; it adds a lovely flavor to drinks or marinades later. Pat the cherries dry with a paper towel. This step is crucial. Moisture can stop the chocolate from adhering later.

In a microwave-safe bowl, combine the semi-sweet chocolate and butter. Melt them together in the microwave, heating in 30-second intervals. Stir in between sessions to ensure even melting. It should result in a luxurious chocolate mixture.

In another bowl, mix the confectioners' sugar, one cup at a time, into the melted chocolate mixture. Add the vanilla extract. Combine until it reaches a smooth, spreadable consistency. This filling is what gives your chocolate cherry a delightful taste and texture.

Using a small spoon, carefully fill each cherry with the chocolate filling. Make sure to fill it generously but avoid overflowing. Place the filled cherries on parchment paper to set.

Once filled, dip each cherry into the remaining melted chocolate mixture, allowing any excess chocolate to drip back into the bowl. Place them back on the parchment paper, ensuring they have enough space to set without touching.

If you're feeling creative, drizzle melted white chocolate over the chocolate-covered cherries for an extra pop of color. Allow everything to set completely. This step may take some time, but the result is worth the wait.