Hi atram

The first penetration problem is primarily due to overfilled vial – no air gab in the vial.
The sample drawing is partly obstructed because of the negative pressure created by the drawing it self.
Try leaving one third of the vial empty. This should reduce the above mentioned effect to a minimum.
If you already purchased starburst septa, as suggested by Alfred88, it should be sufficient because this septum allows air flow into the vial.

Best Regards