Soak a few paper towels and place them in a large bowl. Place the dried figs in the bowl and wrap the wet paper towels over the figs. Try pressing the damp paper towels between each fig.
Microwave the wrapped figs for about 20 seconds. The moisture from the wet paper towels will steam the figs so they unfold and soften up. If some of the figs don’t puff up, gently mold them with your hands so they aren’t folded over or creased anywhere. This will make filling them a lot easier.
Fill a saucepan with about 1 inch of water and bring it to a simmer then turn the heat to low. Place a heat resistant bowl over the saucepan and fill the bowl with 8 oz of semisweet chocolate chips (that’s about 1 1/4 cup). I highly recommend using good quality chocolate. I personally use Guittard in all my baking.
Once you see the chocolate starting to melt, pour 2 tbsp of warm heavy whipping cream over the chocolate. Stir the heavy cream and chocolate until the chocolate is melted.
Add 3 tbsp brandy to the chocolate mixture and stir until smooth. You may want to start off with 2 tbsp and taste to see if you prefer more or less brandy. Everyone likes it different.
Remove the ganache from heat and strain the chocolate through a mesh strainer. This will remove any clumps that might not have fully melted. This is an important step. When piping the ganache into the figs the piping tip will need to be really small, therefore if there are even the smallest little clumps of chocolate, it will clog the piping tip.
Fill a pastry bag with the warm ganache and fill the bottom of each fig using a Wilton #3 piping tip. You might need to slightly puncture the fig with the tip before filling it. A good way to know if the fig is fully filled is if it starts plumping up and the ganache is flowing back from where you started filling it.
Place a cooling rack on a baking sheet and place each filled fig stem side down. Refrigerate for about 1 hour.
Start off by melting about 2 cups of semisweet chocolate in the microwave (in 35-second intervals to prevent scorching). Once the chocolate is completely melted and smooth, pour it into a tall/narrow glass cup.
Using small tongs grab each refrigerated fig by the stem and dip it into the tall glass filled with melted chocolate. Try doing this in one motion.
Once the entire fig is coated, bring it up out of the chocolate and have one hand tap the other hand that is holding the tongs. This will remove any excess chocolate. When these no more chocolate falling, lightly brush the bottom of the dipped fig over the top rim of the cup to remove any extra chocolate. As you near dipping the last few figs, the chocolate may need to be reheated or you might want to melt the remaining 1 cup of semisweet chocolate chips.
Place the chocolate dipped figs stem side up onto a baking sheet lined with parchment paper and refrigerate for 30 minutes. Serve at room temperature.