Pour the sugar, water, corn syrup and vanilla extract into a pot, and set it to medium heat. Stir with a rubber spatula until everything is melted and combined.
Then increase the heat to high, and attach a candy thermometer to the pot. Heat the sugar until it reaches 310F, stirring occasionally.
Fill a bear-shaped silicone mold halfway with the candy mixture. Using a pair of tweezers, stick some shards of coffee lollipops into the melted candy to resemble the stripes of a tiger. Work quickly before the candy sets, but be careful not to burn yourself. Once all of the stripes are in place, pour in the remaining melted candy.
Then stick one lollipop stick into each shape, holding the stick in place until the candy fully sets. This will take around 15-20 minutes. Then gently unmold the lollipops from the mold.
Using a toothpick and some melted dark chocolate, draw on the tiger’s eye, nose and mouth.