A punctum dilating and plug inserting system includes an inserter and a protective cover defining a dilator. The inserter includes a longitudinal body, and a handle. The handle has a rounded stationary member and a trigger rotatably connected to the handle by a living hinge. A mounting wire extends through the body and is connected to the trigger. When the trigger is activated, the wire is retracted and a plug mounted on a distal end of the wire is released. A packaging is provided for receiving, protecting, and handling at least a portion of the entire inserter until ready for use. An end of the packaging includes a dilator dip for dilating the punctum in advance of receiving the punctum plug.