The current research examined whether or not the interface of an extender attached to an assistive device should be identical to the interface of the assistive device. Given the profile of assistive devices such as wheelchairs and the need to extend them in special cases such when maneuvering over rough terrain or obstacles such as stairs and steep inclines, the interface design of these extenders (attached to existing assistive devices) should be evaluated. We have simulated a carrying platform for a wheelchair that is larger than the user’s regular wheelchair. We have examined whether participants used to handling their wheelchair, when asked to operate the carrying platform, handle the latter’s interface better or worse than their wheelchair’s interface. Participants (61) were assigned to one of two between-participants groups. Both groups were trained to navigate a wheelchair using the wheelchair’s interface and then operated the carrying platform. The Familiar Interface group navigated the carrying platform using the wheelchair’s interface, and the New Interface group navigated it with a new interface. The results demonstrated that the Familiar Interface group took longer to perform the task and collided more often with obstacles, compared to the New Interface group. The greater number of collisions can be linked directly to an erroneous mental model of the carrying platform’s size. The insights we reach can be linked to both extenders attached to an assistive device and other technological extenders.