An automated reservoir filling system for a portable medical device is disclosed. The system includes a vial sealed by a septum partially filled with a liquid and a gas occupying a headspace. The system further includes a reservoir with a volume defined between a reservoir septum and a plunger head. The plunger head is coupled to a plunger arm which is further coupled to a drive system. Further included is a transfer system with a vial end that pierces the vial septum and remains in contact with the liquid, and a reservoir end that pierces the reservoir septum and remains in the reservoir volume. A controller coupled to the drive system to actuates the drive system automatically drawing fluid from the vial to the reservoir through the degas system.