Optical coherence tomography (OCT) has revolutionized diagnostics in ophthalmology. However, it requires pa-tient cooperation to fixate on multiple targets and stabilize their head utilizing both chin and forehead rests. Patient cooperation is particularly important for image montaging, where patients are asked to fixate on multiple targets to sequentially image different regions of interest on the retina. These individual volumes are then combined into a single large field of view volume. To automate the OCT image acquisition process, we previously developed a robot-mounted OCT scanner that auto-aligned with the retinal region of interest while compensating for subject motion. We utilized this system to self-align at multiple regions-of-interest and acquire stabilized volumes. We then montaged volume projections into a larger field of view image. The system tracked the 3D location of the subject's eye as well as their gaze orientation using a combination of face and pupil tracking cameras. We demonstrated automated OCT acquisition for live image montaging on free-standing subjects and evaluated the consistency of our live volumetric mapping on human subject data. Our results demonstrate that the system not only stabilized images, but also provided sufficient control of region-of-interest specific alignment to automatically acquire and montage OCT images, synthetically increasing the system's field of view by$20^{\circ}$.