Be careful not to overmix the ice cream when swirling in the caramel sauce.
In a medium saucepan, heat the milk, vanilla bean and scrapings, and pepper. Scald the milk, cover, and remove from heat. Let steep for 30 minutes.
Combine the egg yolks and brown sugar in the bowl of an electric mixer. Beat at medium-high speed until very thick and pale yellow, 3 to 5 minutes. Meanwhile, return the milk to a simmer.
Remove the vanilla bean. Add half the milk to egg-yolk mixture, and whisk until blended. Stir into remaining milk, and cook over low heat, stirring constantly, until mixture thickens enough to coat a spoon.
Remove from heat, and immediately stir in 2 cups cream. Pass mixture through a strainer into a medium bowl set over a large bowl of ice water. Allow to chill.
Meanwhile, dissolve the granulated sugar in 1 cup of water in a heavy-bottomed saucepan. Set over high heat, wash down sides of pan with a pastry brush, and cook, without stirring, until an amber caramel forms, 8 to 10 minutes, swirling the pan occasionally. Remove from heat. Carefully stir in the remaining 1/2 cup cream. Add the vanilla extract, cinnamon, and 8 figs. Let stand about 15 minutes while the mixture cools and figs soften.
Remove from heat, and chill. Puree caramel mixture in a blender or food processor, and set aside.
Freeze ice cream in an ice-cream maker according to manufacturer's instructions. Fold 1 cup of chilled caramel sauce into frozen ice cream, until large swirls of caramel form. Transfer to a plastic container, and freeze for at least 2 hours to harden.
Cut remaining 16 figs in half lengthwise. Combine remaining caramel sauce and figs in a saucepan. Heat over medium heat just until figs are warm, 3 to 5 minutes, and serve warm over the ice cream.