In a small saucepan, combine the drained and finely chopped maraschino cherries, 2 tablespoons granulated sugar, cornstarch, and reserved cherry juice. Cook over medium heat, stirring constantly, until the mixture thickens and comes to a simmer, about 3-5 minutes. Remove from heat and stir in almond extract if using. Let cool completely.

In a medium bowl, whisk together the flour, cocoa powder, baking soda, and salt. Set aside.

In the bowl of a stand mixer fitted with the paddle attachment (or a large bowl with an electric mixer), cream together the softened butter and 1 1/2 cups granulated sugar on medium speed until light and fluffy, about 3-4 minutes.

Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.

Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined and no streaks of flour remain. Do not overmix. Cover the dough and refrigerate for at least 30 minutes to firm up, making it easier to handle.

Preheat oven to 350°F (175°C). Line two baking sheets with parchment paper.

Scoop out dough using a small cookie scoop (about 1.5-2 tablespoons). Roll each portion into a smooth ball. Using your thumb or the back of a spoon, create a deep indentation in the center of each cookie dough ball.

Fill each indentation with approximately 1 teaspoon of the cooled cherry filling. Gently reshape the dough around the filling to enclose it, sealing it completely. If desired, you can leave a little filling exposed for a visual cue.

Place the filled cookie balls about 2 inches apart on the prepared baking sheets. Bake for 10-12 minutes, or until the edges are set and the centers are still slightly soft. Do not overbake.

Let cookies cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely.

While the cookies cool, prepare the glaze. In a heatproof bowl set over a small saucepan of simmering water (a double boiler), combine the chopped dark chocolate, heavy cream, and butter. Alternatively, microwave in short 30-second bursts, stirring in between, until melted and smooth.

Remove from heat and stir in the vanilla extract until smooth and glossy.

Once the cookies are completely cool, dip the tops of each cookie into the chocolate glaze, or drizzle the glaze over the tops using a spoon. Place glazed cookies back on the wire rack (or a sheet of parchment paper) to allow the glaze to set. This may take 30-60 minutes at room temperature, or you can speed it up by refrigerating for 15-20 minutes.