The large apertures of the upcoming generation of Giant Segmented Mirror Telescopes will enable unprecedented angular resolutions that scale as ∝λ/D and higher sensitivities that scale as D4 for point sources corrected by adaptive optics (AO). However, all will have pupil segmentation caused by mechanical struts holding up the secondary mirror (European Extremely Large Telescope and Thirty Meter Telescope) or intrinsically, by design, as in the Giant Magellan Telescope (GMT). These gaps will be separated by more than a typical atmospheric coherence length (Fried Parameter). The pupil fragmentation at scales larger than the typical atmospheric coherence length, combined with wavefront sensors with weak or ambiguous sensitivity to differential piston, can introduce differential piston areas of the wavefront known as “petal modes.” Commonly used wavefront sensors, such as a pyramid wavefront sensor, also struggle with phase wrapping caused by >λ/2 differential piston wavefront error (WFE). We have developed the holographic dispersed fringe sensor (HDFS), a single pupil-plane optic that employs holography to interfere the dispersed light from each segment onto different spatial locations in the focal plane to sense and correct differential piston between the segments. This allows for a very high and linear dynamic piston sensing range of approximately ±10 μm. We have begun the initial attempts at phasing a segmented pupil utilizing the HDFS on the High Contrast Adaptive optics phasing Testbed (HCAT) and the Extreme Magellan Adaptive Optics instrument (MagAO-X) at the University of Arizona. In addition, we have demonstrated the use of the HDFS as a differential piston sensor on-sky for the first time. We were able to phase each segment to within ±λ/11.3 residual piston WFE (at λ=800 nm) of a reference segment and achieved ∼50 nm RMS residual piston WFE across the aperture in poor seeing conditions.