In the bowl of an electric mixer fitted with the paddle attachment, beat the butter and 1/4 cup sugar on medium-high speed until light and fluffy, about 3 minutes. Beat in the eggs and vanilla. Slowly add the flour, baking powder and salt, and beat until combined. Remove dough to a clean work surface. Divide dough into quarters, wrap each in plastic, and chill until firm, about 1 hour.
Remove 1 portion of dough from refrigerator. Between 2 pieces of parchment paper, roll dough out to a 9 by 12-inch rectangle, about 1/8-inch thick. Remove remaining portions of dough from the refrigerator1 at a time, and repeat rolling process. Stack dough between sheets of parchment paper, and place on a baking sheet. Chill until firm, about 10 minutes.
Place 1 rectangle of dough on a baking sheet. Repeat process with a second rectangle of dough. Pipe teaspoon size mounds of plum mixture onto each rectangle of dough in even rows. There should be 15 mounds per baking sheet. Remove remaining 2 rectangles of dough from refrigerator and place 1 over each baking sheet to enclose plum mixture. Let stand until dough softens slightly, about 2 minutes. Lightly press around each mound of plum mixture with your fingertips to seal. Using a fluted pastry wheel, cut dough into squares between mounds of plum mixture forming ravioli. Freeze until firm, about 15 minutes.
Preheat oven to 350 degrees F. Using an offset spatula, separate the ravioli. Sprinkle ravioli with remaining 2 tablespoons sugar. Bake until golden brown, 25 to 30 minutes. Transfer to a wire rack to cool completely.
Place the plums, orange rind and juice, cinnamon, and sugar in a shallow saucepan. Bring to a boil, and reduce heat to a simmer. Cook until the plums are tender, and the liquid has reduced to a glaze, about 45 minutes. Add the cognac, and cook for 5 more minutes, watching carefully as the liquid will thicken rapidly and start to caramelize somewhat.
Transfer plum mixture to a food processor fitted with the metal blade. Add honey. Pulse until the mixture is smooth, 40 seconds. Transfer to a small pastry bag fitted with a coupler.
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