Add 1/2 cup vinegar, brown sugar, cinnamon stick and pinch of salt to the liquid. Simmer until it is thickened and syrupy, 15 to 20 minutes, being careful not to scorch the sauce. Remove from heat and stir in remaining vinegar, allow to cool slightly. Pour reduction into squeeze bottle.
Cut the tenderloin crosswise into 1/2-inch thick slices. Flatten each slice into an oval and slice each oval into 2 strips. Season the strips with salt and pepper - there should be about 40 slices.
Heat the oven to broil with the rack in the center. Place a fig quarter, cut side down, on a slice of pork. Lift up each end of the pork slice around the fig and place seam-side down on sheet pan. Brush with glaze and broil until cooked (3 minutes).
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