An information handling system (IHS) docking system includes an IHS chassis defining an alignment member passageway and an IHS connector opening. An IHS connector is movably coupled to the IHS chassis adjacent the IHS connector opening and resiliently biased into a retracted orientation. An alignment member securing device is moveably coupled to the IHS chassis adjacent the alignment member passageway and resiliently biased into a non-securing orientation. At least one docking actuator is located in the alignment passageway and coupled to the IHS connector and alignment member securing device. When the IHS chassis is docked with a docking station including a docking connector and an alignment member, the alignment member engages the at least one docking actuator to move the IHS connector relative to the IHS chassis to mate with the docking connector, and move the alignment member securing device relative to the IHS chassis to engage the alignment member.